What’s Happening in the Hudson Valley Holidays 2026? 100+ Things to Do
By Brian Caplicki · Caplicki Home Team · Updated November 13, 2026 · 13 min read
Every tree lighting, holiday market, Nutcracker performance, drive-through light show, historic mansion tour, Hanukkah celebration, Santa visit, Christmas tree farm, and New Year’s Eve party across Orange, Ulster, Sullivan, and Dutchess Counties from Nov 13 through December 31, 2026, organized so you can plan the whole season in one sitting.
Every drive-through light show, Nutcracker, mansion tour, tree lighting, Hanukkah celebration, church bazaar, Santa parade, and New Year’s Eve party across Orange, Ulster, Sullivan, and Dutchess Counties from Nov 13 through Dec 31, 2026. Scroll by interest below, or jump to the full calendar further down.
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The full November to December 2026 holiday calendar, mansion tour schedule, Christmas tree farm list, and Nutcracker lineup, all in one printable PDF.
What Are the Biggest Hudson Valley Holiday Events in 2026?
A handful of events pull regional crowds every year and deserve to be on the calendar first.
Bethel Woods Peace, Love & Lights. November 27, 2026 through January 2, 2027. Bethel (12720). 1.7-mile drive-through light show on the original 1969 Woodstock site, 5 to 10 p.m. nightly with last entry at 9. Standard vehicles around $27. Runs every night except Christmas Eve and Christmas Day. New drone show elements on select evenings. This is the Hudson Valley’s biggest holiday light attraction.
Mohonk Mountain House Christmas Celebration. December 23 to 25, 2026. New Paltz (12561). Three-day Victorian holiday weekend at the castle on the lake. Christmas Day Grand Buffet, ice skating in the pavilion, Nutcracker ballet selections, a theatrical A Christmas Carol, outdoor Winter Lights, self-guided tree and gingerbread tour. Overnight package only. (877) 724-3159.
The Three Nutcrackers. Three different ballet companies, three different venues, three consecutive weekends. Sugar Loaf PAC runs Warwick Dance Collective’s Nutcracker December 4 to 6 with live orchestra. UPAC in Kingston hosts Catskill Ballet Theatre’s 41st annual production December 11 to 13. Bardavon in Poughkeepsie closes out with New Paltz Ballet Theatre’s 30th annual December 12 to 13, featuring guest New York City Ballet dancers.
Historic Mansion Holiday Tours. Four Hudson Valley mansions open for the Gilded Age Christmas season on November 27. Staatsburgh (Mills Mansion) runs through December 30 by timed reservation. Locust Grove in Poughkeepsie runs through December 20, then reopens daily December 26 to 30. Wilderstein in Rhinebeck opens for tours Friday, Saturday, and Sunday through December 27. Boscobel (just over the Dutchess line in Garrison) runs Holiday Twilight Tours November 27 through December 12.
Woodstock Christmas Eve on the Green. Thursday December 24, 2026. Village Green, Woodstock (12498). Caroling at 5 p.m., Santa arrives at 5:30. A 90-plus year Woodstock tradition. Stockings handed out to every child.
City of Middletown Tree Lighting & Parade. Friday November 27, 2026. Downtown Middletown (10940). Orange County’s biggest holiday kickoff, directly on Black Friday.
Millbrook Parade of Lights. Friday December 4, 2026. Lineup 5:30 p.m., parade steps off 7 p.m. from Franklin Ave, Millbrook (12545). Illuminated fire trucks, Santa & Mrs. Claus, village storefronts.
Browse by Interest
Where Are the Best Hudson Valley Christmas Light Displays in 2026?
Bethel Woods Peace, Love & Lights. Nov 27 to Jan 2, 2027. Bethel (12720). The region’s biggest drive-through light show. 1.7 miles, 5 to 10 p.m. nightly (last entry 9), closed Dec 24 and 25. Around $27 per standard vehicle. New drone show elements on select evenings. This is the one most Hudson Valley families do every year.
A Frosty Fest. 778 Broadway (Rt 9W), Ulster Park (12487). Opens Nov 27. Drive-through light display from the team behind Headless Horseman. Smaller and more playful than Bethel Woods, closer to Kingston for Ulster/Dutchess families.
Watt Christmas Wonderland. Goshen (10924). Open nightly November 27 through December 27, 6 to 9 p.m. 21st season of a beloved Goshen tradition. $10 donation per vehicle, cash only. 845-294-3391.
Wonderland of Lights at Dutchess County Fairgrounds. Rhinebeck (12572). Annual drive-through show. 2026 dates not yet published as of early November; 2025 ran November 28 to December 28, 5 to 9 p.m., $25 to $32 per car. Check thewonderlandoflights.com.
Mohonk Winter Lights. Resort grounds, New Paltz. Overnight guests only, tied to the Victorian Holidays and Christmas Celebration period.
Bruschi Christmas. Wallkill (12589). Long-running family-run residential light show, reportedly running November 24 through January 1, 2027. 15,000+ lights synced to music. Check their Facebook for nightly hours. Free walk-through.
Where Are the Best Hudson Valley Christmas Tree Farms in 2026?
Most Hudson Valley cut-your-own tree farms open the day after Thanksgiving and run until they sell out, typically mid-to-late December. Reservations are increasingly standard at the bigger farms. Call ahead.
Orange County:
| Emmerich Tree Farm | Warwick (10990). Cut-your-own, 12 varieties. Reservations required. 845-986-0151. |
| Edward’s Family Farm | Warwick (10990). Cut-your-own + pre-cut, wreaths. 845-986-1330. |
| Rocky Bar Farm | Westtown (10998). Douglas fir, white and blue spruce, gift shop. 845-988-5313. |
| Farmside Acres | Cornwall (12518). Cut-your-own. Free cider, donuts, candy canes. 845-534-7996. |
| Hoeffner Farms | Montgomery (12549). Cut-your-own + pre-cut, wreaths, poinsettias. 845-457-3453. |
| Manza Family Farm | Montgomery (12549). Cut-your-own + pre-cut. Christmas shop, hot cocoa. 845-361-2965. |
| Pierson’s Farm | Middletown (10940). Cut-your-own + pre-cut. Wreath-making class, Winter Fest market. 845-343-1232. |
| Pine View Farm | New Windsor (12553). Cut-your-own, pre-cut, wreaths. 845-562-0069. |
| Stone Oak Farm | Slate Hill (10973). Cut-your-own + pre-cut. Hot cocoa. 845-355-7966. |
| Graney’s Tree Farm | Pine Bush / Crawford (12566). Cut-your-own blue spruce, balsam wreaths. 845-744-5609. |
Ulster County:
| Bell’s Christmas Trees | Accord (12404). Cut-your-own firs and spruces. 845-626-7849. |
| Balsam Ridge | Clintondale (12515). Fraser, Balsam, Canaan, Concolor fir, Blue Spruce. 845-883-7206. |
| Wallkill View Farm | New Paltz (12561). Pre-cut and wreaths, farm market. 845-255-8050. |
| Christmas Tree Lane | Wallkill (12589). Cut-your-own and pre-cut, wreaths. 845-895-2347. |
Sullivan County:
| Maplehorst Farm | Monticello (12701). Cut-your-own + fresh-cut, hayrides. 845-794-8596. |
| Friendly Acres Farm | Cochecton (12726). 25+ year operation, hot cocoa. |
| Pine Farm | Youngsville (12791). Cut-your-own, small weekends-only farm. |
Dutchess County:
| Battenfeld’s | Red Hook (12571). Cut-your-own, Santa visits, wagon rides, Christmas shop. 845-758-8018. |
| Hahn Farm | Salt Point (12578). Hayrides to tree field, refreshments, free saws. 845-266-3680. |
| Abel’s Tree Farm | Verbank (12585). Trees up to 13 ft, small-farm feel. 845-677-6395. |
| Primrose Hill Farm | Staatsburg (12580). White/Norway spruce, Douglas/Concolor fir. 845-889-4725. |
| Solvang Tree Farm | Poughkeepsie (12603). Cut-your-own + fresh-cut, family operation. 845-227-5591. |
| Big Rock Farms | Stanfordville (12581). Balsam fir, white pine, Norway spruce. 845-868-7432. |
| Murphy Crest | Amenia (12501). Weekends only, 10 a.m. to 4 p.m. 845-373-9388. |
| Evergreen Farm | Millbrook (12545). Only two weekends. Go early. 845-677-8000. |
| Fishkill Farms | Hopewell Junction (12533). Pre-cut Balsam fir, wreaths. Santa visits, cider donuts. 845-897-4377. |
Which Hudson Valley Mansions Are Decorated for the Holidays in 2026?
Staatsburgh (Mills Mansion) – A Gilded Age Christmas. Staatsburg (12580). November 27 through December 30, Thursday through Sunday by timed-entry reservation (closed Dec 24, 25, 31). (845) 889-8851.
Locust Grove (Samuel Morse Estate). Poughkeepsie (12601). November 27 through December 20 Thursday through Sunday 9 a.m. to 5 p.m., then daily December 26 to 30.
Wilderstein. Rhinebeck (12572). November 27 through December 27, Friday/Saturday/Sunday at noon, 1, 2, and 3 p.m. $20 at the door. Closed Christmas Day.
Boscobel Holiday Twilight Tours. Garrison. November 27 through December 12. Technically Putnam County but a long-standing Hudson Valley tradition.
Mount Gulian Historic Site. Beacon (12508). Annual pattern mid-to-late December. 2026 dates to be confirmed; (845) 831-8172.
Vanderbilt Mansion National Historic Site. Hyde Park (12538). Open daily through December 31 except Christmas Day. $15 tour.
Where Can You See The Nutcracker in the Hudson Valley in 2026?
Sugar Loaf PAC – The Nutcracker. December 4 to 6, 2026. Sugar Loaf (10981). Warwick Dance Collective with Sugar Loaf Arts Collective live orchestra. Fri 7 p.m., Sat noon and 5 p.m., Sun 2 p.m.
UPAC – Catskill Ballet Theatre’s 41st Annual Nutcracker. December 11 to 13, 2026. Ulster Performing Arts Center, 601 Broadway, Kingston (12401). Fri 7 p.m., Sat 4 p.m., Sun 2 p.m. Tickets $45 adult, $30 kids/students/seniors.
Bardavon – New Paltz Ballet Theatre’s 30th Season Nutcracker. December 12 to 13, 2026. Bardavon 1869 Opera House, 35 Market St, Poughkeepsie (12601). Sat 2 p.m. and 7:30 p.m., Sun 3 p.m. Features New York City Ballet guest dancers. $40 adult / $35 members and students.
What Hudson Valley Holiday Concerts and Theater Shows Should You See in 2026?
Jimmy Sturr’s The Magic of Christmas. Paramount Theatre, Middletown (10940), Saturday December 5 at 3 p.m. The polka legend’s annual Christmas show. $41 to $47.
Northern Dutchess Symphony: Sounds of the Season (Santa Baby!). Rhinebeck HS auditorium (12572), Saturday December 5, 4 to 6 p.m. $10 to $45.
Warwick Valley Chorale Holiday Concert. Albert Wisner Public Library, Warwick (10990), Saturday December 5, 2 to 4 p.m. Cap 100, registration required.
Bethel Woods Hootenanny Sing-Alongs. Fridays December 4, 11, and 18, Bethel (12720).
A Christmas Carol by Ulster Dance Company. UPAC, Kingston (12401), Sunday December 6.
Hudson Valley Baroque: Musical Friends – A Holiday Celebration. Historic Huguenot Street, New Paltz (12561), Sunday December 13, 2 to 3 p.m.
Jessica Lynn: A Very Merry Classic Christmas. Paramount Middletown Dec 18 at 7 p.m., UPAC Kingston Dec 19.
Slambovian Circus of Dreams – A Very Slambovian Christmas. Towne Crier Cafe, 379 Main St, Beacon (12508), Saturday December 19 at 8 p.m. Around $35.
Hudson Valley Symphony Orchestra: Handel’s Messiah. Skinner Hall, Vassar College, Poughkeepsie. Annual pattern mid-to-late December; 2026 date to be confirmed.
Where Can You See Santa in the Hudson Valley in 2026?
Walkway Over the Hudson Holiday on the Walkway with Santa. Highland (12528). Sunday November 29, 12 to 3 p.m. Free. Candy canes and music at the Ulster Welcome Center plaza.
Battenfeld’s Christmas Tree Farm Santa Visits. Red Hook (12571). Weekends from Black Friday through Christmas while you pick a tree.
Fishkill Farms Santa Weekends. Hopewell Junction (12533). Weekends from Thanksgiving through mid-December. Santa visits paired with cider donuts and the orchard shop.
Brunch with Santa at Bear Mountain Inn. Bear Mountain (10911). Saturdays and Sundays, 9 a.m. to 2 p.m. throughout December (2025 ran through Dec 21, 2026 dates to be posted at visitbearmountain.com). $48 adults, $28 kids 4 to 12. Reservations required. One of the most-loved Hudson Valley holiday family traditions.
Catskill Mountain Railroad Polar Express. Kingston (12401). Select dates November 13 through December 30. 70-minute ride with Santa and a keepsake sleigh bell for every child. Tickets $38 to $55.
Galleria at Crystal Run. Middletown (10941). Santa photo experience daily through Christmas Eve (reservations open now). Two special Santa events confirmed for 2026: Santa Cares sensory-friendly event Sunday Dec 6 (an inclusive experience for children with sensory needs), and Santa Pet Night Monday Dec 7, 5 to 7 p.m., and Monday Dec 14, 4 to 7 p.m. hosted with Cherry Hill Programs and the Humane Society.
Woodbury Common Premium Outlets. Central Valley (10917). Santa in the Market Hall from mid-November through Christmas Eve, with Simon’s formal Santa arrival ceremony (sleigh and reindeer) typically the Friday after Thanksgiving. 2026 schedule publishes at the mall’s site.
Poughkeepsie Galleria. Poughkeepsie (12601). Santa in Center Court from late November through Christmas Eve, hosted by Cherry Hill Programs. A Santa Cares sensory-friendly session typically runs a weekend morning in early December; 2026 date to be posted.
Newburgh Mall. Newburgh (12550). Santa photos through Christmas Eve. 2026 schedule to be posted on the mall’s events page.
Where Can You Take the Kids for Holiday Fun in 2026?
Bear Mountain Ice Rink. Bear Mountain State Park (10911). Public skating sessions Friday, Saturday, and Sunday through the holiday season. $5 admission, $10 skate rental. (845) 786-2701 x266.
Middletown Tree Lighting & Parade. Friday November 27. Downtown Middletown (10940). Orange County kickoff.
Millbrook Parade of Lights. Friday December 4 at 7 p.m. Millbrook (12545). Illuminated fire trucks, Santa and Mrs. Claus.
Saugerties Firetruck Parade of Lights. Annual pattern first Sunday of December. Saugerties (12477). Date to be confirmed.
Rhinebeck Parade of Lights. Saturday December 5 around 5 p.m. Rhinebeck (12572).
Historic Newburgh Holiday Light Parade. Newburgh (12550). Fourth annual. 2026 date to be confirmed.
Sugar Loaf Old Fashioned Christmas. The Sugar Loaf artisan hamlet (10981). Annual pattern mid-December Saturday. Horse-drawn carriages, strolling carolers, open studios, Santa visit, and holiday shopping in the historic craft village.
Washingtonville Christmas Parade. Annual pattern early December Saturday. Washingtonville (10992). Date to be confirmed.
Good Grief! It’s Whoville in Washingtonville. Sat Dec 5, 9 a.m. Washingtonville (10992). Family holiday morning event.
Great Chanukah Squishfest. 94 Gilbert Street, Monroe (10950), Sun Dec 6, 4 p.m. Family Chanukah celebration.
What Are the Hanukkah Events in the Hudson Valley in 2026?
Hanukkah 2026 runs from sundown Friday December 4 through Saturday December 12. Chabad centers in Kingston, Newburgh, New Paltz, and Poughkeepsie typically do public menorah lightings on the first and/or final nights; confirm locally.
Bethel Woods Menorah Lighting Celebration. Sunday December 6, 4 p.m. Bethel (12720). With Chabad Jewish Monticello.
Rhinebeck Community Menorah Lighting. Saturday December 5. Paired with the Holiday Shop Crawl and tree lighting. Rhinebeck (12572).
Saugerties Community Menorah Lighting. Annual pattern first Sunday in December. Reis parking lot. Saugerties (12477). Date to be confirmed.
Light Up Hyde Park: A Chanukah Celebration. Hyde Park (12538). Annual pattern. 2026 date to be confirmed.
Which Hudson Valley Holiday Markets Should You Shop in 2026?
Christkindl Markt. Germania Poughkeepsie (12601). Friday and Saturday, November 20 to 21. Traditional German market, heated outdoor tent.
Hudson Valley Hullabaloo. Andy Murphy Midtown Neighborhood Center, Kingston (12401). Saturday and Sunday, November 21 to 22. 70+ makers. $2 cash at the door; kids 12 and under free.
Bethel Woods Holiday Market. November 27 to 29 (main weekend). Pop-up Saturdays December 5, 12, and 19. Bethel (12720). Free admission and parking. 17th annual.
Hudson Valley Artisan Marketplace at Locust Grove. November 27 to 29. Poughkeepsie (12601). 12th annual juried craft show.
DCC Foundation Holiday Craft Fair. November 28 to 29. Dutchess Community College, Poughkeepsie (12601). Juried, 100+ artists.
Dutchess Handmade Pop-Up at Arts Mid-Hudson. Poughkeepsie. Monday through Saturday, October 22 through December 16. Closed Thanksgiving and Veterans Day.
Pierson’s Farm Winter Fest Market. Middletown (10940). Early December.
Which Hudson Valley Church Holiday Fairs Should You Shop in 2026?
Church bazaars and holiday fairs are some of the best-loved and most reliable traditions in the Hudson Valley. Handmade crafts, cookie walks, bake sales, raffles, Santa visits, and the kind of hyperlocal community events you won’t find on any county tourism calendar. Most are free admission; luncheons and food sales are typically a few dollars. Parish committees usually publish dates only 4 to 8 weeks out, so verify directly before you go.
Orange County:
| Orange County Holiday Fair Trail | Sat Nov 21 (pattern). Four-church passport day: Grace Episcopal Middletown, First Presbyterian Goshen, St. James’ Episcopal Goshen, United Church of Middletown. Fish & chips lunch at Grace. $100 gift card drawing. |
| OLMM North Pole Bazaar | Our Lady of the Miraculous Medal. Sat Nov 21, 10 a.m. to 3 p.m. Confirmed 2026. |
| Visitation BVM Christmas Bazaar | Weekend before Thanksgiving (Nov 21–22 pattern). |
| St. Stephen the First Martyr | Warwick (10990). Christmas Market & Craft Fair, first weekend of December. Gently used and new Christmas décor, Nativity Tour, Trucks & Trees. |
| St. Jude Parish | Monroe (10950). First Saturday of December, 10 a.m. to 4 p.m. |
| Cornwall Community Church | Cornwall. Children’s shopping room, Attic Treasures, basket raffle. |
| St. Mary’s Most Sacred Heart | Port Jervis. St. Nicholas Faire, early December. |
Ulster County:
| Reformed Church of New Paltz | 92 Huguenot St, New Paltz (12561). Holiday Fair & Soup on the Stoop. First Fri evening + Sat of Dec. |
| New Paltz UMC Cookie Walk | Homemade holiday cookies sold by the pound. Early-to-mid December. |
| St. Augustine’s Highland | Flavors of the World Christmas Market & Toy Drive. Early December. |
| Saugerties UMC Holiday A-Fair | Saugerties (12477). Fri & Sat mid-November. |
| Immanuel Lutheran Kingston | Christmas Handcrafted & Gift Boutique. |
| St. James UMC Kingston | Star in the Valley Christmas Market & Cookie Caper. |
| United Reformed Bloomington | Christmas Bazaar, jewelry and bake sale. Early December. |
Sullivan County:
Parish fairs in Sullivan County tend to be small and under-posted online. The strongest known community anchors are the Callicoon Holiday Tree Lighting at the Train Depot (Sat Nov 28 at 5 p.m.) and Dickens on the Delaware in Callicoon (Sat Dec 12). First Presbyterian in Monticello runs a Cookie Stop/Bake Sale in early-to-mid December. Check bulletins at Immaculate Conception (Liberty), Sacred Heart (Jeffersonville), and St. Francis Xavier (Narrowsburg) directly.
Dutchess County:
| Grace Church Millbrook | St. Nicholas Bazaar. Sat mid-December, 10 a.m. to 2 p.m. Fine crafts and cookie sale. |
| New Hackensack Reformed | Wappingers Falls (12590). 50th annual Piggy Bank Bazaar for Children. First Sat of Dec, 9 a.m. to noon. |
| St. Joachim–St. John Beacon | St. Joachim’s School Gym, Beacon (12508). Two-day Christmas Fair, Sat 9 a.m. to 3 p.m., Sun 8:30 a.m. to 2 p.m. Santa visits. |
| St. Mary School Fishkill | Holiday Craft Fair, early-to-mid November Saturday. |
| Rhinebeck Reformed Cookie Walk | 6368 Mill St, Rhinebeck (12572). Second Sun of Dec in Cordes Hall. 40+ varieties sold by the pound. |
| Elizaville UMC | 740 County Route 2 (12523). First Sat of Dec, 9 a.m. to 3 p.m. |
| St. James’ Hyde Park | 4526 Albany Post Rd (12538). Cookie & Candy Sale, early Dec Sat 10 a.m. to 2 p.m. |
| UMC of Hyde Park | Annual Craft Fair, early-to-mid Nov Sat 10 a.m. to 4 p.m. |
Browse by Date
Here is the full calendar from Thanksgiving weekend to New Year’s Eve. Town tree lightings that had not yet published their 2026 date at the time of writing are labeled “date to be confirmed” with the recurring annual pattern noted.
What’s Happening in the Hudson Valley Before & Through Thanksgiving Weekend 2026?
The holiday season starts quietly, with the pre-Thanksgiving church bazaars and craft fairs the weekend of November 21, then explodes on Black Friday when Bethel Woods, A Frosty Fest, Peace Love & Lights, the historic mansion tours, and the first round of village tree lightings all open together.
| Sun Nov 15 | Hudson Valley Baroque: Music for the Home. Historic Huguenot Street, New Paltz (12561), 2 p.m. Third of four concerts this season. |
| Sun Nov 22 | Christmas Magic: Free Community Photo Booth. 46 Main St, Warwick (10990), 11 a.m. Family holiday photo booth. |
| Nov 20–21 | Christkindlmarkt Port Jervis. Downtown Port Jervis (12771). 100+ vendors, traditional German holiday market. |
| Fri–Sat Nov 20–21 | Saugerties United Methodist Holiday A-Fair. Saugerties (12477). Pattern-confirmed; date to be confirmed. |
| Sat Nov 21 | Orange County Holiday Fair Trail. Four-church passport day with $100 gift card drawings. Grace Episcopal Middletown, First Presbyterian Goshen, St. James’ Episcopal Goshen, and United Church of Middletown all host fairs the same Saturday. Pattern-confirmed; verify date. |
| Sat Nov 21 | Our Lady of the Miraculous Medal North Pole Bazaar & Bistro. 10 a.m. to 3 p.m. Confirmed 2026. |
| Nov 21–22 | Visitation BVM Annual Christmas Bazaar. Weekend before Thanksgiving; parish posted a 2026 placeholder, verify closer to date. |
| Nov 25–29 | Mohonk Mountain House Thanksgiving Holiday. New Paltz (12561). Resort-wide Thanksgiving programming. |
| Thu Nov 26 | Mid-Hudson Road Runners Turkey Trot. Arlington HS, Lagrangeville (12540). 5-mile, 2-mile, 25K, kids 1-mile. Bib pickup at Fleet Feet Poughkeepsie. |
| Thu Nov 26 | Woodstock Turkey Trot. Village center, Woodstock (12498). 5K. First 125 registrants get a 2026 tote. |
| Fri Nov 27 | Bethel Woods Peace, Love & Lights opens. Bethel (12720), 5 to 10 p.m. Opening night of the big drive-through light show. Runs through January 2. |
| Fri Nov 27 | A Frosty Fest opens. 778 Broadway (Rt 9W), Ulster Park (12487). Drive-through light display from the Headless Horseman team. |
| Fri Nov 27 | Watt Christmas Wonderland opens. Goshen (10924), 6 to 9 p.m. nightly through Dec 27. 21st season. $10/vehicle cash only. |
| Fri Nov 27 | City of Middletown Tree Lighting & Parade. Downtown Middletown (10940). Orange County kickoff. |
| Fri Nov 27 | Warwick Fire Department Tree Lighting. Lewis Park, Village of Warwick (10990), 6 p.m. Paired with Operation Toy Train food and toy drive. |
| Fri Nov 27 | Tin Barn Brewing Black Friday Super-Bash + Tree Lighting. Sugar Loaf / Chester (10918), 6:30 p.m. The Georgia 5 80s Dance Party. |
| Fri Nov 27 | Woodstock Lighting of the Square. Village Green, Woodstock (12498), 7 p.m. (Real Woodstock). |
| Sat Nov 28 | Incidental Contact at Tin Barn Brewing. Sugar Loaf / Chester (10918), 6 p.m. Thanksgiving weekend show. |
| Nov 27–29 | Bethel Woods Holiday Market. Fri & Sat 11 a.m. to 7 p.m., Sun 12 to 6 p.m. 17th annual. Free admission and parking. Bethel (12720). |
| Fri Nov 27 | Wilderstein Holiday House Tours open. Rhinebeck (12572). Fri/Sat/Sun at noon, 1, 2, and 3 p.m. through Dec 27. $20 at door. Closed Christmas Day. |
| Fri Nov 27 | Staatsburgh “A Gilded Age Christmas” opens. Mills Mansion, Staatsburg (12580). Thu–Sun by timed reservation through Dec 30. Closed Dec 24, 25, 31. |
| Fri Nov 27 | Locust Grove Holiday Tours open. Poughkeepsie (12601). Thu–Sun 9 a.m. to 5 p.m. through Dec 20, then daily Dec 26–30. |
| Fri Nov 27 | Boscobel Holiday Twilight Tours open. Garrison. Runs through Dec 12. Technically Putnam County but a long-standing Hudson Valley holiday tradition. |
| Nov 27–29 | Hudson Valley Artisan Marketplace at Locust Grove. 12th annual juried craft show. Poughkeepsie (12601). |
| Nov 28–29 | DCC Foundation Holiday Craft Fair. Dutchess Community College, Poughkeepsie (12601). Juried, 100+ artists. |
| Sun Nov 29 | Walkway Over the Hudson Holiday on the Walkway with Santa. Ulster Welcome Center Plaza, Highland (12528), 12 to 3 p.m. Seasonal music and candy canes. |
| Sat Nov 28 | Callicoon Holiday Tree Lighting. At the Train Depot, Callicoon (12723), around 5 p.m. |
What’s Happening Early December (Nov 30–Dec 6, 2026)?
The first week of December is when nearly every Hudson Valley village lights its tree. Most towns do it the first Friday or Saturday. Hanukkah begins at sundown on Thursday December 4.
| Fri Dec 4 | Hanukkah begins at sundown. Candle lighting through Dec 12. |
| Fri Dec 4 | Millbrook Parade of Lights. Lineup 5:30 p.m., parade 7 p.m. from Franklin Ave, Millbrook (12545). Illuminated fire trucks, Santa & Mrs. Claus. |
| Fri Dec 4 | Friends of Mills Winter Wonderland Gala. Mills Mansion, Staatsburg (12580). Annual benefit evening. |
| Dec 4–6 | Sugar Loaf PAC: The Nutcracker. Warwick Dance Collective with live orchestra. Fri 7 p.m., Sat noon & 5 p.m., Sun 2 p.m. Sugar Loaf (10981). |
| Fri Dec 4 | Bethel Woods Hootenanny Sing-Along. First of three Friday night sing-alongs during Peace, Love & Lights. |
| Sat Dec 5 | Rhinebeck Holiday Shop Crawl + Tree & Menorah Lighting. Shop Crawl 3 to 5 p.m. with carolers, tree and menorah lighting follows at the municipal lot, Parade of Lights around 5 p.m. Rhinebeck (12572). |
| Sat Dec 5 | Jimmy Sturr’s The Magic of Christmas. Paramount Theatre, 17 South St, Middletown (10940), 3 p.m. Polka legend. Tickets $41 to $47. |
| Sat Dec 5 | Northern Dutchess Symphony: Sounds of the Season (Santa Baby!). Rhinebeck HS auditorium (12572), 4 to 6 p.m. Tickets $10 to $45. |
| Thu Dec 3 | Piece by Piece: Puzzle Competition, Holiday Edition. Albert Wisner Public Library, Warwick (10990), 6 p.m. |
| Sat Dec 5 | Multicultural Holiday Storytime. Albert Wisner Public Library, Warwick (10990), 11 a.m. to noon. |
| Sat Dec 5 | Warwick Valley Chorale Holiday Favorites. Albert Wisner Public Library, Warwick (10990), 2 to 4 p.m. Registration required, cap 100. |
| Sun Dec 6 | Elmendorph Inn Holiday Open House. Red Hook (12571). Historic 18th-century inn decked out for the holidays. |
| Sat Dec 5 | Bethel Woods Holiday Market Pop-Up #1. 2 to 9 p.m. Free. Bethel (12720). |
| Fri Dec 4 | Kingston Snowflake Festival. Uptown Kingston (12401), 6 to 8 p.m. Hosted by KUBA (Kingston Uptown Business Association). |
| Sat Dec 5 | Illuminate Goshen Holiday Market, Tree Lighting & Light Parade. Downtown Goshen (10924). Goshen Parks & Rec + Goshen Fire Department + Illuminate Goshen + Goshen Chamber. |
| Sat Dec 5 | Washingtonville Christmas Parade (16th Annual). Lineup 4 p.m., parade 6 p.m. Blooming Grove Chamber. Washingtonville (10992). |
| Sat Dec 5 | Good Grief! It’s Whoville in Washingtonville. 9 a.m. Washingtonville (10992). Family holiday morning event. |
| Sat Dec 5 | Newburgh Celebrates Christmas. Historic Newburgh Riverfront (12550), 1 p.m. |
| Sat Dec 5 | Old Hyde Park Annual Home Tour. Hyde Park (12538), 10 a.m. Historic district holiday home tour. |
| Sun Dec 6 | Bethel Woods Menorah Lighting Celebration. Bethel (12720), 4 p.m. With Chabad Jewish Monticello. |
| Sun Dec 6 | A Christmas Carol by Ulster Dance Company. UPAC, Kingston (12401). |
| Sun Dec 6 | YMCA 43rd Annual Reindeer Ramble. Kingston (12401). Family run/walk. |
| Sun Dec 6 | Saugerties Holiday in the Village & Firetruck Parade of Lights (annual pattern). Tree and menorah lighting at Reis parking lot around 5 p.m., fire truck parade to Seamon Park. Saugerties (12477). Date to be confirmed. |
| Sun Dec 6 | Hyde Park Merry & Bright: Holiday Market. Across from Town Hall, 4390 Albany Post Rd, Hyde Park (12538), 2 to 6 p.m. |
| Sun Dec 6 | Hyde Park Merry & Bright: Parade of Lights + Tree Lighting. Line-up at Hyde Park Drive-In 4 p.m., parade 5 p.m. to Town Hall, tree lighting 6 p.m. with Santa, refreshments, crafts. Hyde Park (12538). |
| Sun Dec 6 | Newburgh Holiday Light Parade (4th Annual). Downtown Newburgh (12550), 6 p.m. Historic Newburgh, Inc. |
| Sun Dec 6 | Great Chanukah Squishfest. 94 Gilbert Street, Monroe (10950), 4 p.m. Family Chanukah celebration. |
| Sun Dec 6 | Santa Cares Sensory-Friendly Event. Galleria at Crystal Run, Middletown (10941). Inclusive Santa photo experience for children with sensory needs. |
| Fri–Sat Dec 4–5 | Reformed Church of New Paltz Annual Holiday Fair & Soup on the Stoop. 92 Huguenot St, New Paltz (12561). Fri 5 to 8 p.m., Sat 9 a.m. to 2 p.m. Crafts, wreaths, poinsettias, bake sale, Santa visit, caroling. |
| Dec 5–6 | St. Stephen the First Martyr Christmas Market & Craft Fair. 228 West St, Warwick (10990). Paired with Nativity Tour and Trucks & Trees. Gently used and new Christmas décor. |
| Sat Dec 5 | St. Jude Parish Annual Christmas Fair. Monroe (10950), 10 a.m. to 4 p.m. Snow date Sunday. |
| Sat Dec 5 | Cornwall Community Church Christmas Fair. Cornwall. Crafts, bake sale, Attic Treasures, children’s shopping room, basket raffle. |
| Sat Dec 5 | New Hackensack Reformed 50th Annual Piggy Bank Bazaar for Children. Wappingers Falls (12590), 9 a.m. to noon. Fiftieth year. |
| Dec 5–6 | St. Joachim–St. John the Evangelist Christmas Fair. St. Joachim’s School Gym, Beacon (12508). Sat 9 a.m. to 3 p.m., Sun 8:30 a.m. to 2 p.m. Crafts, raffles, baked goods, Santa. |
| Sat Dec 5 | Elizaville United Methodist Church Christmas Bazaar. 740 County Route 2, Elizaville (12523), 9 a.m. to 3 p.m. |
| Sat Dec 5 | St. James’ Episcopal Cookie & Candy Sale. 4526 Albany Post Rd, Hyde Park (12538), 10 a.m. to 2 p.m. Proceeds support outreach ministry. |
| Sat Dec 5 | Pleasant Valley Festival of Lights Parade (annual pattern). Pleasant Valley (12569). |
What’s Happening Hanukkah Week (Dec 7–13, 2026)?
Hanukkah continues through Saturday Dec 12. Two Nutcrackers run back-to-back, Catskill Ballet at UPAC and New Paltz Ballet at Bardavon. Historic Huguenot Street hosts its annual community tree lighting. And the second round of Bethel Woods pop-ups keeps the market scene going.
| Mon Dec 7 | Santa Pet Night. Galleria at Crystal Run, Middletown (10941), 5 to 7 p.m. Pet photos with Santa, hosted by Cherry Hill Programs and the Humane Society. |
| Dec 11–13 | Catskill Ballet Theatre: The Nutcracker (41st annual). UPAC, 601 Broadway, Kingston (12401). Fri 7 p.m., Sat 4 p.m., Sun 2 p.m. Tickets $45 adult, $30 kids/students/seniors. |
| Fri Dec 11 | Bethel Woods Hootenanny Sing-Along #2. Bethel (12720). |
| Dec 12–13 | New Paltz Ballet Theatre: The Nutcracker (30th season). Bardavon, 35 Market St, Poughkeepsie (12601). Sat 2 p.m. & 7:30 p.m., Sun 3 p.m. Features NYC Ballet guest dancers. $40 adult / $35 members and students. |
| Sat Dec 12 | Bethel Woods Holiday Market Pop-Up #2. 2 to 9 p.m. Free. Bethel (12720). |
| Sat Dec 12 | Wintering: A Stillness Experience. Good Work Institute, Kingston (12401). Limited seating winter solstice workshop. |
| Sun Dec 13 | Hudson Valley Baroque: Musical Friends – A Holiday Celebration. Historic Huguenot Street, New Paltz (12561), 2 to 3 p.m. |
| TBD | New Paltz Community Tree Lighting at Historic Huguenot Street (annual pattern). Paper lantern parade at 6:45 p.m. from the Reformed Church to Deyo House lawn, tree lit at 7 p.m. New Paltz (12561). Date to be confirmed. |
| TBD | Light Up Hyde Park: A Chanukah Celebration (annual pattern). Hyde Park (12538). Date to be confirmed. |
| Sat Dec 12 | Grace Episcopal Church St. Nicholas Bazaar. Millbrook (12545), 10 a.m. to 2 p.m. Fine crafts and cookie sale. |
| Sat Dec 12 | Sugar Loaf Old Fashioned Christmas (annual pattern). The Sugar Loaf artisan hamlet (10981). Horse-drawn carriages, strolling carolers, shopping at the open studios, visit from Santa. Date to be confirmed. |
| Sat Dec 12 | Dickens on the Delaware. Callicoon (12723). Victorian-themed street festival. |
| Sun Dec 13 | Rhinebeck Reformed Church Cookie Walk. 6368 Mill St, Rhinebeck (12572), 11 a.m. to 2 p.m. Cordes Hall. 40+ varieties of homemade holiday cookies sold by the pound. |
What’s Happening Mid-December (Dec 14–20, 2026)?
The last full week before Christmas. Mansion tours wind down, the final Bethel Woods pop-ups happen, and Towne Crier in Beacon gets its one Slambovian Christmas show.
| Mon Dec 14 | Santa Pet Night. Galleria at Crystal Run, Middletown (10941), 4 to 7 p.m. Second Santa Pet Night of the season. |
| Fri Dec 18 | Jessica Lynn: A Very Merry Classic Christmas. Paramount Theatre, 17 South St, Middletown (10940), 7 p.m. |
| Fri Dec 18 | Bethel Woods Hootenanny Sing-Along #3. Bethel (12720). |
| Sat Dec 19 | Slambovian Circus of Dreams: A Very Slambovian Christmas. Towne Crier Cafe, 379 Main St, Beacon (12508), 8 p.m. Tickets around $35. |
| Sat Dec 19 | Bethel Woods Holiday Market Pop-Up #3. 2 to 9 p.m. Free. Bethel (12720). |
| Sat Dec 19 | Jessica Lynn: A Very Merry Classic Christmas. UPAC, Kingston (12401). |
| Dec 14–20 | Mount Gulian Historic Site Holiday Tours (annual pattern). Beacon (12508). $15 adult, $12 senior, $8 youth. Date to be confirmed. |
| Dec 14–20 | Hudson Valley Symphony Orchestra: Handel’s Messiah (annual pattern). Skinner Hall, Vassar, Poughkeepsie. Date to be confirmed. |
| Thu Dec 10 | Holiday Centerpieces Workshop. Albert Wisner Public Library, Warwick (10990), 6 p.m. |
| Sun Dec 20 | Locust Grove last day Thu–Sun tours. Reopens daily Dec 26 to 30. |
| Sun Dec 20 | Staatsburgh / Mills Mansion last day Thu–Sun tours. Reopens daily Dec 26 to 30. |
What’s Happening Christmas Week (Dec 21–27, 2026)?
The week of Christmas. Mohonk’s big three-day Christmas Celebration anchors the week. Woodstock does its 90-year-old Christmas Eve on the Green tradition. Mansion tours reopen the day after Christmas.
| Dec 23–25 | Mohonk Victorian Christmas Celebration. 1000 Mountain Rest Rd, New Paltz (12561). Christmas Day Grand Buffet, ice skating in the pavilion, Nutcracker selections, A Christmas Carol theatrical, outdoor Winter Lights. Overnight package only. (877) 724-3159. |
| Thu Dec 24 | Woodstock Christmas Eve on the Green. Village Green, Woodstock (12498). Caroling 5 p.m., Santa arrives 5:30. Stockings handed out to every child. 90+ year tradition. |
| Thu Dec 24 | Terrapin Rhinebeck Christmas Eve dinner. 6426 Montgomery St, Rhinebeck (12572), 5 to 9 p.m. |
| Thu Dec 24 | Peace, Love & Lights closed. Also closed Dec 25. |
| Dec 26–30 | Locust Grove daily holiday tours. Poughkeepsie (12601). 9 a.m. to 5 p.m. |
| Dec 26–30 | Staatsburgh / Mills Mansion daily holiday tours. Staatsburg (12580). By timed reservation. |
| Sun Dec 27 | Wilderstein last day of Holiday House Tours. Rhinebeck (12572). |
What’s Happening New Year’s Eve in the Hudson Valley (Dec 28–31, 2026)?
Two destination parties bookend the Hudson Valley on New Year’s Eve: Mohonk Mountain House in New Paltz and Resorts World Catskills in Monticello. Peace, Love & Lights also runs every night through January 2, so if you want to drive through lights instead of going to a party, you can.
| Thu Dec 31 | Mohonk New Year’s Eve Celebration. 1000 Mountain Rest Rd, New Paltz (12561). Resort package. |
| Thu Dec 31 | Resorts World Catskills NYE: The Georgia 5 80s New Year’s Eve Party. Bar 360, Thompson/Monticello (12701), 9 p.m. |
| Thu Dec 31 | Peace, Love & Lights. Open through Jan 2. Bethel (12720). |
| Thu Dec 31 | A Frosty Fest. Ulster Park (12487). Open through late December; confirm end date on site. |
Thinking About Moving to the Hudson Valley in 2027?
This guide exists because the people who end up buying or selling homes in the Hudson Valley tend to be the ones who show up for the tree lightings, the Nutcracker, and Christmas Eve on the Green. If that sounds like you (or someone you know), the Caplicki Home Team would love to help.
Brian Caplicki leads the Caplicki Home Team at Keller Williams HVU, based in Middletown, NY, serving Orange County, Sullivan County, Ulster County, Dutchess County, and the broader Hudson Valley. Reach Brian at 845-656-4498 or brian@caplickihometeam.com.
Sources: bethelwoodscenter.org, bardavon.org, middletownparamount.com, sugarloafpacny.com, warwickperformingarts.com, mohonk.com, wilderstein.org, millsfriends.org, boscobel.org, huguenotstreet.org, woodstockchristmaseve.com, walkway.org, rwcatskills.com, destinationdutchess.com, visitulstercountyny.com, sullivancatskills.com, hvmag.com, chronogram.com, kingstonhappenings.org, each tree farm’s own site or Facebook. Compiled November 13, 2026.
Event dates and times are subject to change without notice. Confirm with each event organizer directly before traveling. Town tree lightings in particular are often announced only 2 to 3 weeks before the event. Last updated November 13, 2026.
Brian Caplicki leads the Caplicki Home Team at Keller Williams HVU, based in Middletown, NY, serving Orange County, Sullivan County, Ulster County, Dutchess County, and the broader Hudson Valley. Reach Brian at 845-656-4498 or brian@caplickihometeam.com.
