May 19, 2026

What’s Happening Memorial Day Weekend 2026 in the Hudson Valley?

By Brian Caplicki · Caplicki Home Team · Updated May 19, 2026 · 6 min read

Memorial Day weekend is when the Hudson Valley wakes up for the season. Here is a county-by-county guide to parades, festivals, and standout events across Orange, Ulster, Dutchess, and Sullivan counties from Friday May 22 through Monday May 25, 2026.

Quick Answer

Memorial Day weekend 2026 across the Hudson Valley features small-town parades on Monday May 25, the Woodstock-New Paltz Art and Crafts Fair all three days, the Sugar Loaf Spring Festival on Saturday and Sunday, the Bearsville Bluegrass Festival on Sunday afternoon, a sunset flag-changing ceremony on the Walkway Over the Hudson, and the Washingtonville carnival running all weekend.

The weather forecast for the region is typical late-May Hudson Valley: mild days, cool evenings, possible scattered showers. Plan for outdoor parades and pack layers.

The Hudson Valley does Memorial Day weekend the way it does everything else, which is locally, sincerely, and with food. Every village has its own parade. Every farm market is opening for the season. The carnivals roll into town. The art fairs set up tents. Whether you live here, are visiting for the long weekend, or are scouting the region as a place you might one day call home, this is one of the best weekends of the year to see the four counties at their friendliest.

Below is a day-by-day agenda that mixes counties so you can plan your weekend by date, followed by deeper county-by-county detail.

What is happening each day of Memorial Day weekend 2026 in the Hudson Valley?

Here is the full schedule, hour by hour, across all four counties. Times are approximate and subject to change. Confirm with the host or village before traveling.

Friday, May 22 (Day 1)

Friday is the warm-up. The Washingtonville Memorial Weekend Carnival is already underway (it opened Thursday May 21) and runs through Monday at L. Vern Allen Park in Orange County. Most parades and festivals start Saturday. Use Friday evening to grab dinner at a Hudson Valley farm-to-table restaurant, walk the Walkway Over the Hudson at sunset in Dutchess County, or pick up groceries for the weekend at the season-opening farmers markets across all four counties.

Time	Event	County
5:00pm to 10:00pm	Washingtonville Memorial Weekend Carnival, L. Vern Allen Park	Orange
10:00am to 6:00pm	Storm King Art Center, New Windsor (last entry 5pm)	Orange

Saturday, May 23 (Day 2)

Saturday is the busiest day on paper. Three of the weekend's flagship events all run simultaneously: the Woodstock-New Paltz Art and Crafts Fair opens at the Ulster County Fairgrounds, the Sugar Loaf Spring Festival fills the artisan village in Orange County, and the Titanic Dinner sets off for Bannerman Island in the evening. If you can only pick one day to be out and about, pick this one.

Time	Event	County
10:00am to 5:30pm	Woodstock-New Paltz Art & Crafts Fair, Ulster County Fairgrounds, New Paltz	Ulster
10:00am to 5:00pm	Sugar Loaf Spring Festival, Sugar Loaf Village	Orange
10:00am to 6:00pm	Storm King Art Center, New Windsor (last entry 5pm)	Orange
12:00pm to 1:30pm	Washingtonville Carnival sensory-friendly preview, L. Vern Allen Park	Orange
3:00pm to 10:00pm	Washingtonville Memorial Weekend Carnival, L. Vern Allen Park	Orange
11:00am to 6:00pm	Hudson-Berkshire Wine & Food Festival, Columbia County Fairgrounds, Chatham (just over Dutchess line)	Columbia (drive-over)
2:00pm to 5:00pm	Warwick Valley Winery & Distillery live music in tasting room	Orange
5:00pm to 10:30pm	Titanic Dinner on Bannerman Island (ticketed, limited to 40 guests)	Dutchess

Sunday, May 24 (Day 3)

Sunday is the most musical day of the weekend. The Bearsville Bluegrass Festival headlines the afternoon in Woodstock, and the day closes with the Walkway Over the Hudson sunset flag-changing ceremony in Highland and Poughkeepsie. The art fair and the Sugar Loaf festival are still going. A natural pairing: Sugar Loaf or the art fair in the morning, Bearsville in the afternoon, the Walkway at dusk.

Time	Event	County
10:00am to 5:30pm	Woodstock-New Paltz Art & Crafts Fair, New Paltz	Ulster
10:00am to 5:00pm	Sugar Loaf Spring Festival, Sugar Loaf Village	Orange
10:00am to 6:00pm	Storm King Art Center, New Windsor	Orange
11:00am to 5:00pm	Hudson-Berkshire Wine & Food Festival, Columbia County Fairgrounds, Chatham (just over Dutchess line)	Columbia (drive-over)
12:00pm to 6:00pm	Bearsville Bluegrass Festival, Bearsville Center, Woodstock (gates 11:30am)	Ulster
Morning	Rhinebeck Farmers Market, Beacon Farmers Market, Warwick Valley Farmers Market	Dutchess + Orange
2:00pm to 5:00pm	Warwick Valley Winery & Distillery live music	Orange
3:00pm to 10:00pm	Washingtonville Memorial Weekend Carnival, L. Vern Allen Park	Orange
7:30pm	Memorial Day Flag-Changing Sunset Ceremony, Walkway Over the Hudson	Dutchess

Monday, May 25 (Memorial Day)

Monday is parade day. Most of the four-county schedule is packed into the morning, with ceremonies running roughly 10:00am to 11:00am at locations large and small. If you cannot pick, find the closest one and walk over with your neighbors. The afternoon is the soft landing: the art fair finishes its run, Storm King and the carnival are still open, and Drowned Lands Brewery in Warwick caps the weekend with a Memorial Day pig roast.

Time	Event	County
10:00am	Hyde Park Memorial Day Parade, Old Hyde Park Dr.	Dutchess
10:00am	Millerton Memorial Day Parade & Ceremony, Veterans Park, 48 Main St.	Dutchess
10:00am	Monticello Flags for Heroes Ceremony, Sullivan County Government Center	Sullivan
10:30am	Unionville Memorial Day Parade, Main St. (service at 11am, Unionville Cemetery)	Orange
10:30am (lineup)	Montgomery Memorial Day Parade, Wallkill Ave. near Grange Hall	Orange
10:30am	Rhinebeck Memorial Day Parade & Ceremony, Mulberry St. to Rhinebeck Cemetery	Dutchess
10:30am	Liberty Memorial Day Parade, Main St. to Liberty Veterans Cemetery	Sullivan
11:00am	Bethel / Kauneonga Lake Memorial Day Service, Veterans Park	Sullivan
11:00am	Millbrook Memorial Day Parade & Ceremony, Franklin Ave. & Tribute Gardens Park	Dutchess
11:00am	Dutchess County Memorial Day Ceremony, John K. Rinaldi Memorial Park, Poughkeepsie	Dutchess
~11:00am	Warwick Memorial Day Parade, Village Hall to Veterans Memorial Park	Orange
Morning	Goshen Memorial Day Parade & Services (confirm step-off time)	Orange
Morning	Newburgh Memorial Day Parade (confirm date and step-off time)	Orange
1:00pm	Sullivan County Veterans Cemetery Service & Wreath Laying, 181 Sunset Lake Rd., Liberty	Sullivan
10:00am to 5:30pm	Woodstock-New Paltz Art & Crafts Fair (closing day)	Ulster
10:00am to 6:00pm	Storm King Art Center, New Windsor (open Memorial Day)	Orange
Afternoon	Drowned Lands Brewery Memorial Day Pig Roast, Warwick	Orange
2:00pm to 8:00pm	Washingtonville Memorial Weekend Carnival, L. Vern Allen Park (closing day)	Orange

Times in burgundy are the marquee events of each day. All times are local Eastern. Confirm with the host before traveling.

What is happening in Orange County NY this Memorial Day weekend?

Orange County packs the most range into the weekend. You can be eating a corn dog under midway lights in Washingtonville, browsing pottery in Sugar Loaf, walking the sculptures at Storm King, and standing on Main Street watching a parade all in the same 72 hours.

Sugar Loaf Spring Festival takes over the artisan village of Sugar Loaf on Saturday May 23 and Sunday May 24 from 10am to 5pm. Free, two days, rain or shine. Expect live music, local vendors, food trucks, a beer garden, a dog-friendly area, and a kids zone.

The Washingtonville Memorial Weekend Carnival, hosted by the Washingtonville Knights of Columbus and featuring McDaniel Brothers Shows, runs Thursday May 21 through Monday May 25 at L. Vern Allen Park (intersection of State Route 94 and Ahern Blvd). Hours are Thursday and Friday 5pm to 10pm, Saturday 3pm to 10pm with a sensory-friendly preview from 12pm to 1:30pm, Sunday 3pm to 10pm, and Monday 2pm to 8pm. $30 daily wristbands buy unlimited rides, or separate tickets are available each day. For sponsorship or more info, contact Vincent Saldana at 845-401-1004.

Memorial Day parades on Monday May 25 anchor the weekend in Orange County. The Goshen Memorial Day Parade and Services runs through the heart of the village. The Warwick Memorial Day Parade steps off from Village Hall on Main Street and winds out to the Warwick Cemetery and Veterans Memorial Park. The Unionville Memorial Day Parade steps off Main Street at 10:30am, with a service at the Unionville Cemetery at 11am. The Montgomery Memorial Day Parade lines up at 10:30am on Wallkill Avenue near the Grange Hall, with refreshments at Veterans Memorial Park after. Newburgh also hosts a Memorial Day parade between Second Street and Union Avenue. Step-off times can shift year to year, so check your village website or VFW post before you head out.

Storm King Art Center in New Windsor is open Wednesday through Monday, 10am to 6pm, with final entry at 5pm. The 500-acre open-air sculpture park is open on Memorial Day. Advance tickets are recommended for holiday weekends.

For a relaxed Memorial Day Monday, Drowned Lands Brewery in Warwick is hosting a Memorial Day pig roast on May 25 with whole roasted pigs, a la carte backyard barbecue, pulled pork, and cold beer.

What is open in Ulster County NY for Memorial Day weekend 2026?

Ulster County's weekend is anchored by two events that have been running for decades and still pull crowds from across the region.

The Woodstock-New Paltz Art and Crafts Fair returns to the Ulster County Fairgrounds at 249 Libertyville Road in New Paltz, NY from Saturday May 23 through Monday May 25, 10am to 5:30pm each day. More than 200 juried artists from across the country, a children's tent with supervised crafts, ongoing craft demonstrations, live entertainment, and Hudson Valley food and drink. Admission is $12 for adults, $10 for seniors, and free for kids 12 and under. Parking is free. This one is worth showing up early on Saturday before the lines build.

The Bearsville Bluegrass Festival returns Sunday May 24 from 12pm to 6pm (gates at 11:30am) at Bearsville Center, 277 Tinker Street in Woodstock. The 2026 lineup features On the Trail with Austin Scelzo, Catskill Mountain String Band, and Bugs on a Log String Band. Advance tickets are $25 or two for $45, with VIP seating available. Children are free. A Wernick Method Jam Class runs that morning from 10am to noon for pickers.

If you are looking for the most distinctive Saturday night in the Hudson Valley, the Titanic Dinner on Bannerman Island on Saturday May 23 from 5pm to 10:30pm recreates the legendary 11-course First Class RMS Titanic menu, prepared by six Hudson Valley chefs and limited to 40 guests. Tickets are $450 and period-accurate dress is encouraged. Boat departure is from the Hudson River.

Ulster County does not hold a major Memorial Day parade this year in either Kingston or New Paltz. For ceremony-style observances, neighboring Dutchess County and Orange County offer the closest options. Use Monday morning to head into the Bearsville/Woodstock area for the art fair's closing day or to wander Kingston's Stockade District at your own pace.

Where are the Dutchess County Memorial Day parades and ceremonies?

Dutchess County's Memorial Day weekend leans civic and historic, with one of the most moving sunset ceremonies in the region.

On Sunday May 24 at 7:30pm, the Walkway Over the Hudson State Historic Park hosts a Memorial Day flag-changing ceremony at the flagpole, lasting roughly 30 minutes. The ceremony features a four-gun salute, the playing of Taps, local artists performing God Bless America, and a carnation toss into the Hudson River, hosted by Pleasant Valley American Legion Post 739. Park early. Walk out as the sun goes down. It is the kind of evening people remember years later.

On Monday May 25, Dutchess County holds its main Memorial Day ceremony at 11am at the Dutchess County War Memorial at John K. Rinaldi Memorial Park, at Raymond Avenue and Main Street in the Town of Poughkeepsie.

Smaller village parades fill the morning. The Hyde Park Memorial Day Parade steps off at 10am from Old Hyde Park Drive at 4114 Albany Post Road. The Rhinebeck Memorial Day Parade and Ceremony begins at 10:30am from Mulberry Street and concludes at Rhinebeck Cemetery, hosted by American Legion Post 429. The Millbrook Memorial Day Parade and Ceremony starts at 11am at Franklin Avenue and Tribute Gardens Park. The Millerton Memorial Day Parade begins at 10am at Veterans Park, 48 Main Street.

If you want the full Dutchess long weekend, the parade circuit pairs naturally with a stop at a Rhinebeck or Millbrook restaurant for brunch and an afternoon walk at Vanderbilt Mansion or Mills-Norrie State Park.

What is happening in Sullivan County NY Memorial Day weekend?

Sullivan County's Memorial Day weekend is quieter and ceremonial, which is part of its charm. If you are looking to slow down and be somewhere green, this is the county to head into.

On Monday May 25, the Town of Liberty Memorial Day Parade runs down Main Street at 10:30am and concludes with a ceremony at the Liberty Veterans Cemetery on Cold Spring Road, hosted by the Town of Liberty and Corporal Russell Sprague VFW Post 109. At 1pm, the Sullivan County Veterans Service Agency holds a Memorial Day Service and Wreath Laying Ceremony at the Sullivan County Veterans Cemetery, 181 Sunset Lake Road in Liberty.

In Monticello at 10am, the Sullivan Central Rotary Club hosts a Flags for Heroes ceremony at the Sullivan County Government Center, with a Color Guard. In Bethel, the SGT Andrew Brucher-Bailey-Richman VFW Post 5499 holds a small service at 11am at Veterans Park, across from the Kauneonga Lake Fire House.

Around the official ceremonies, the rest of Sullivan County is opening for the season. Catskills hiking trails, the Sullivan County rail trails, and the lake towns around Kauneonga Lake and White Lake are easy day trips from anywhere in the Hudson Valley.

Where can you eat, drink, and get outside this Memorial Day weekend in the Hudson Valley?

The parades and festivals get the headlines, but the real character of a Hudson Valley Memorial Day weekend often shows up at a tasting room bar, a farm stand, or a trailhead. Here is what is open across the four counties.

Wineries, cideries, and distilleries open Memorial Day weekend

Orange County is home to Brotherhood Winery at 100 Brotherhood Plaza Drive in Washingtonville, which holds the title of America's oldest continuously operating winery (founded 1839) and offers daily tastings, tours of the historic stone cellars, and live music on weekends. Warwick Valley Winery & Distillery at 114 Little York Road in Warwick has live music in the tasting room every weekend from 2pm to 5pm. Angry Orchard Cider House at 2241 Albany Post Road in Walden is the region's largest cider tasting room, set on a 60-acre orchard with a treehouse bar, weekend events, and food. And as covered above, Drowned Lands Brewery in Warwick is doing a Memorial Day pig roast on Monday May 25.

Ulster County is the heart of the Shawangunk Wine Trail, a roughly 60-mile loop linking nine wineries between the Shawangunk Mountains and the Hudson River. Highlights include Whitecliff Vineyard & Winery in Gardiner and Robibero Family Vineyards at 714 Albany Post Road in New Paltz. The trail does not host a special trail-wide event Memorial Day weekend (their next group event is Summer Sip in July), but all member wineries are open for weekend tastings. Bad Seed Cider Company at 43 Baileys Gap Road in Highland runs a year-round tasting room with food trucks and live music and is a popular stop after a day at the Walkway.

If you want to make a day of crossing the Hudson, the Hudson-Berkshire Wine & Food Festival runs Saturday May 23 (11am to 6pm) and Sunday May 24 (11am to 5pm) at the Columbia County Fairgrounds in Chatham, just over the Dutchess County line. The festival features wineries, distilleries, cideries, and farm vendors from across the Hudson-Berkshire Beverage Trail.

Farmers markets and farm stands

Memorial Day weekend is the moment Hudson Valley farmers markets hit full stride. The Goshen Farmers Market opened May 15 and runs Fridays in the heart of the village. The Rhinebeck Farmers Market opened May 3 and runs Sundays. The Warwick Valley Farmers Market runs Sunday mornings. The Beacon Farmers Market runs year-round on Sundays. River-town markets in Newburgh, Cornwall, Port Jervis, Saugerties, and Kingston are also open. Expect early-season greens, asparagus, ramps, the last of the spring rhubarb, and a lot of plant starts for home gardens.

For farm stands, Lawrence Farms Orchards in Newburgh has its farm market open with bedding plants, baked goods, and early-season produce, though U-pick strawberry fields typically do not open until early-to-mid June in the Hudson Valley. Kelder's Farm in Kerhonkson (Ulster) is similar. Strawberry season is just around the corner, not quite here.

Outdoor and family destinations

The Walkway Over the Hudson State Historic Park is open all weekend (with Sunday's sunset ceremony already noted above). Bear Mountain State Park on the Hudson River in Orange County is a classic Memorial Day destination for families. Minnewaska State Park Preserve in Ulster County opens its trails to hikers, swimmers (at Lake Minnewaska's beach later in the season), and rock climbers. Mohonk Preserve in Gardiner offers some of the best ridge hiking in the Northeast. Mills-Norrie State Park and the Vanderbilt Mansion National Historic Site in Dutchess County are both open and excellent paired with a Rhinebeck or Hyde Park parade.

In Sullivan County, the Bethel Woods Center for the Arts museum and grounds at the historic 1969 Woodstock concert site in Bethel are open Memorial Day weekend (the pavilion concert season opens the following weekend with Ann Wilson on May 29 and Hardy on May 30). The Sullivan County rail trails and the lake towns around Kauneonga Lake and White Lake make for an easy slow-down afternoon.

How should you plan a Memorial Day weekend Hudson Valley tour?

If you are local, pick a parade close to home Monday morning and build the rest of the weekend around an art fair or festival. If you are visiting from out of the area, base yourself somewhere central. New Paltz, Goshen, and Rhinebeck each put you within an hour of almost everything on this list. Saturday is the day to do the Woodstock-New Paltz fair and Sugar Loaf back to back. Sunday is the day for Bearsville Bluegrass and the Walkway sunset ceremony. Monday is the day to pick your parade.

If you are scouting the Hudson Valley as a place you might one day call home, this weekend is genuinely the best one of the year to do it. You will see the towns, the people, the parks, and the pace of life all in 72 hours. If you want a local realtor who knows the difference between living in Goshen, Warwick, New Paltz, Rhinebeck, and Liberty, I'm always happy to grab a coffee while you are up here.

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Hudson Valley Memorial Day Weekend 2026 FAQ

What is happening each day of Memorial Day weekend 2026 in the Hudson Valley?

Friday May 22 is a light day with the Washingtonville Carnival and Storm King open. Saturday May 23 brings the Woodstock-New Paltz Art and Crafts Fair, the Sugar Loaf Spring Festival, and the Titanic Dinner on Bannerman Island. Sunday May 24 features the Bearsville Bluegrass Festival in Woodstock and the Walkway Over the Hudson sunset flag-changing ceremony. Monday May 25 is parade day across all four counties, with the Dutchess County main ceremony at 11am in Poughkeepsie.

What is open in the Hudson Valley on Memorial Day weekend 2026?

Storm King Art Center is open Wednesday through Monday from 10am to 6pm and is open on Memorial Day Monday May 25, 2026. The Woodstock-New Paltz Art and Crafts Fair runs all three days of the weekend at the Ulster County Fairgrounds. Most county and town parades, ceremonies, restaurants, farmers markets, and the Walkway Over the Hudson are open across Orange, Ulster, Dutchess, and Sullivan counties.

Where are the Memorial Day parades in Orange County NY?

Multiple villages in Orange County NY host Memorial Day parades on Monday May 25, 2026, including Goshen, Warwick, Unionville (10:30am, Main Street), Montgomery (10:30am lineup at Wallkill Avenue), and Newburgh. Step-off times vary, so confirm with the local village office or VFW post before heading out.

What is the Woodstock-New Paltz Art and Crafts Fair?

The Woodstock-New Paltz Art and Crafts Fair is a juried fair held twice a year at the Ulster County Fairgrounds in New Paltz, NY. The Memorial Day 2026 edition runs Saturday May 23 through Monday May 25 from 10am to 5:30pm, with more than 200 artists, a children's tent, craft demonstrations, live entertainment, and Hudson Valley food and drink. Admission is $12 for adults, $10 for seniors, and free for kids 12 and under. Parking is free.

Is the Walkway Over the Hudson open Memorial Day weekend?

Yes. The Walkway Over the Hudson State Historic Park is open Memorial Day weekend. A special Memorial Day flag-changing sunset ceremony is held on Sunday May 24, 2026 at 7:30pm and runs about 30 minutes, featuring a four-gun salute, Taps, and a carnation toss into the Hudson River, hosted by Pleasant Valley American Legion Post 739 at the flagpole.

What family-friendly events are happening in Orange County NY May 22-25, 2026?

Family-friendly options include the Washingtonville Memorial Weekend Carnival at L. Vern Allen Park (rides, games, food all weekend), the Sugar Loaf Spring Festival on Saturday May 23 and Sunday May 24 from 10am to 5pm with live music, vendors, and a kids zone, and Storm King Art Center in New Windsor with open-air sculpture across 500 acres.

What time is the Bearsville Bluegrass Festival in Woodstock 2026?

The Bearsville Bluegrass Festival is on Sunday May 24, 2026 from 12pm to 6pm at Bearsville Center, 277 Tinker Street, Woodstock NY. Gates open at 11:30am. Advance tickets are $25, two for $45, with VIP seating available. Children are admitted free.

What time is the Dutchess County Memorial Day ceremony in Poughkeepsie?

Dutchess County's main Memorial Day ceremony is on Monday May 25, 2026 at 11am at the Dutchess County War Memorial at John K. Rinaldi Memorial Park, at the intersection of Raymond Avenue and Main Street in the Town of Poughkeepsie.

Are there Memorial Day parades in Sullivan County NY 2026?

Yes. Sullivan County events on Monday May 25, 2026 include the Liberty Memorial Day Parade at 10:30am on Main Street, the Sullivan County Veterans Cemetery service at 1pm on Sunset Lake Road in Liberty, the Monticello Flags for Heroes ceremony at 10am at the Sullivan County Government Center, and a Bethel area service at 11am at Veterans Park across from the Kauneonga Lake Firehouse.

What Hudson Valley wineries and cideries are open Memorial Day weekend 2026?

All Shawangunk Wine Trail wineries in Orange and Ulster counties are open for weekend tastings, including Whitecliff Vineyard in Gardiner and Robibero Family Vineyards in New Paltz. Brotherhood Winery in Washingtonville (America's oldest winery, established 1839) offers daily tastings, tours, and live music. Warwick Valley Winery & Distillery has live music every weekend 2pm to 5pm. Angry Orchard Cider House in Walden and Bad Seed Cider Company in Highland are both open. Drowned Lands Brewery in Warwick hosts a Memorial Day pig roast on Monday May 25.

Can you pick strawberries in the Hudson Valley Memorial Day weekend 2026?

Probably not yet. U-pick strawberry fields in the Hudson Valley typically open in early-to-mid June, not Memorial Day weekend. Farm markets at places like Lawrence Farms Orchards in Newburgh and Kelder's Farm in Kerhonkson are open with bedding plants, baked goods, and early-season produce, but the U-pick fields themselves are usually still a couple of weeks off. Strawberry festivals in the region typically run mid-to-late June.

Are there state parks and hiking trails open Memorial Day weekend in the Hudson Valley?

Yes. Bear Mountain State Park (Orange), Minnewaska State Park Preserve and Mohonk Preserve (Ulster), Mills-Norrie State Park and the Vanderbilt Mansion grounds (Dutchess), the Walkway Over the Hudson, and the Sullivan County rail trails are all open Memorial Day weekend 2026. State parks are open for hiking, picnicking, and most amenities, though some beaches and swimming areas may not open until later in the season.

Sources

Event details compiled from local government and organizer sources, current as of May 19, 2026. Confirm individual step-off and start times with the host before traveling.

The Caplicki Home Team is a Keller Williams HVU real estate team based in Middletown, NY, serving Orange County, Ulster County, Dutchess County, Sullivan County, and the broader Hudson Valley. Reach Brian at 845-656-4498 or brian@caplickihometeam.com.

What’s Happening Memorial Day Weekend 2026 in the Hudson Valley?