Vineyard brunches, a cider festival in Callicoon, scenic train rides out of Kingston, and a community day at Opus 40. Here's exactly where to spend Mother's Day weekend across Orange, Sullivan, and Ulster counties.
Spring is the moment the Hudson Valley wakes back up. Orchards are flowering, the wineries reopen their patios, the train whistles start running on weekends again, and Mother's Day weekend is when most of our towns roll out their best foot. If you're looking for the best things to do in the Hudson Valley this weekend (May 8 through May 10, 2026), this is your shortlist for Orange County, Sullivan County, and Ulster County, all in one place.
Mother's Day falls on Sunday, May 10 this year, so most events lean into brunch, gardens, music, and family-friendly outdoor time. A few are bookable, a few are walk-up, and a couple are first-come-first-served. I've sorted them by county so you can pick the radius that fits your day.
What's happening in Orange County NY this weekend?
Orange County is brunch country on Mother's Day, and the field is deep this year.
Mother's Day Brunch by the Vineyard at Christopher Jacobs Winery at Pennings Vineyard in Pine Bush is the standout. Brunch starts at noon (food at 12:30), it includes a wine tasting plus a glass of wine, and guitarist Andrew Mercer plays from 1 to 4 p.m. It's $70 per couple and the views from the vineyard are about as good as it gets in Orange County in May.
The Venue at Winding Hills Golf Club in Montgomery runs three Mother's Day seatings (10 a.m., 12:30 p.m., and 2:45 p.m.) with a complimentary mimosa, an omelet station, and a carving station, all overlooking the course.
The Stagecoach Inn in Goshen is doing a 10 a.m. to 4 p.m. brunch buffet with breakfast classics, a carving station, and one mimosa per adult included. It's $75 for adults, $25 for kids, and the patio side of the historic inn is one of the prettiest spots in the village.
Villa Venezia in Middletown is running their popular Mother's Day brunch buffet at $68 per adult and $30 per child, with the full classic spread Villa Venezia is known for. Call for reservations.
If you want a non-brunch outing, Sugar Loaf Performing Arts Center in Chester has "A Man Called Otto" on Friday May 8 and the Almost Queen tribute concert on Saturday May 9. Two very different evenings, depending on whether you want a movie night or a Queen sing-along.
What's happening in Sullivan County NY this weekend?
Sullivan County's marquee event is the Catskills Cider Fest, returning for its second year on Saturday, May 9, 2026 at Seminary Hill Orchard and Cidery in Callicoon. The lineup includes Brooklyn Cider House, Nine Pin, and a strong bench of regional cider producers. If your idea of a perfect Hudson Valley Saturday is hard cider, an apple orchard view, and a slow drive home along the Delaware, this is the one.
Up the road in Jeffersonville, Liberty Blooms West has just opened, and the village of Liberty has had a steady run of weekend pop-ups, food, and live music throughout May. Sullivan Catskills tourism is leaning hard into "May in the Catskills" weekends this year, so several restaurants in Livingston Manor, Callicoon, and Jeffersonville are running Mother's Day specials worth calling ahead for.
Quieter but worth it: spring trout fishing on the Willowemoc and Beaverkill is in full swing, and the trails at Mongaup Pond and Sundown Wild Forest are usually empty on Sunday morning if you want a hike with mom.
What's happening in Ulster County NY this weekend?
Ulster County may have the most variety of the three counties this weekend.
Opus 40 Community Day happens Saturday, May 9 in Saugerties from 11 a.m. to 3 p.m. This year is the big one: it's a 50th-anniversary celebration honoring founder Harvey Fite's life and legacy. Expect guided tours of the iconic bluestone sculpture park, local makers, and live music. It's a great pick if you want something cultural without sitting still.
Twin Star Orchards in New Paltz is running a Mother's Day Market on May 9 and 10. Local artisan gifts, wood-fired pizzas out of the brick oven, and hard ciders on the lawn. This is the easy answer if you have an indecisive group, because you can shop, eat, and drink without leaving the property.
For Mother's Day brunch in Ulster, The River Pavilion at Hutton Brickyards in Kingston is doing a prix-fixe brunch on Sunday, May 10 from 11 a.m. to 6 p.m., with bottomless bubbles, live music, and unfiltered Hudson River views. It books up, so call early.
If your mom is the train, museum, or vintage type, the Catskill Mountain Railroad is running scenic rides out of Kingston on Saturday with departures at 11 a.m., 1 p.m., and 3 p.m. The ride threads the Esopus Creek and the Catskill foothills, and it's about as low-stress an outing as you can plan with a multi-generational group.
Hudson Valley weekend events at a glance
Here's the quick reference, sorted by county and date.
| Event | Town | County | Date |
|---|---|---|---|
| Mother's Day Brunch by the Vineyard (Pennings) | Pine Bush | Orange | Sun, May 10 |
| Winding Hills Mother's Day Brunch | Montgomery | Orange | Sun, May 10 |
| Stagecoach Inn Brunch | Goshen | Orange | Sun, May 10 |
| Villa Venezia Mother's Day Buffet | Middletown | Orange | Sun, May 10 |
| Sugar Loaf PAC: Almost Queen tribute | Chester | Orange | Sat, May 9 |
| Catskills Cider Fest at Seminary Hill | Callicoon | Sullivan | Sat, May 9 |
| Opus 40 Community Day (50th anniversary) | Saugerties | Ulster | Sat, May 9 |
| Twin Star Orchards Mother's Day Market | New Paltz | Ulster | Sat-Sun, May 9-10 |
| Catskill Mountain Railroad Scenic Rides | Kingston | Ulster | Sat, May 9 |
| Hutton Brickyards Mother's Day Brunch | Kingston | Ulster | Sun, May 10 |
Sources: Visit Orange County NY tourism, Sullivan Catskills tourism, Ulster County tourism, and venue websites, as of May 4, 2026. Always confirm dates and pricing directly with the venue before you go.
A few tips before you head out
Mother's Day brunches in the Hudson Valley book out fast, so reserve before Friday if you haven't already. Pennings, Winding Hills, The Stagecoach Inn, Villa Venezia, and Hutton Brickyards all run multiple seatings and they fill from the inside out. For the cider fest in Callicoon and Opus 40 in Saugerties, get there at the door rather than mid-afternoon. Parking and lines are gentlest in the first hour. And if mom likes a slow morning, the 1 p.m. Catskill Mountain Railroad departure is the easiest one to make from anywhere in Orange or Ulster County.
Hudson Valley Real Estate FAQ
What are the best Mother's Day weekend events in the Hudson Valley in 2026?
Top picks for Mother's Day weekend (May 8-10, 2026) include the Mother's Day Brunch by the Vineyard at Pennings Vineyard in Pine Bush (Orange County), Catskills Cider Fest at Seminary Hill in Callicoon (Sullivan County), Opus 40 Community Day in Saugerties (Ulster County), and a Mother's Day Market at Twin Star Orchards in New Paltz.
Where is the best Mother's Day brunch in Orange County NY?
Strong Orange County NY Mother's Day brunch options include Christopher Jacobs Winery at Pennings Vineyard in Pine Bush ($70 per couple, includes wine tasting and live music), The Venue at Winding Hills Golf Club in Montgomery (three seatings with omelet and carving stations), The Stagecoach Inn in Goshen ($75 adults, $25 kids, includes a mimosa), and Villa Venezia in Middletown ($68 per adult buffet).
What's happening in Sullivan County NY this weekend?
Sullivan County's headline event is the second annual Catskills Cider Fest at Seminary Hill Orchard and Cidery in Callicoon on Saturday, May 9, 2026, featuring Brooklyn Cider House, Nine Pin, and other regional cideries. Liberty and Jeffersonville also have spring shopping and dining specials happening throughout the weekend.
What is there to do in Ulster County NY on Mother's Day weekend?
Ulster County standouts include Opus 40 Community Day in Saugerties on Saturday, May 9 (a 50th-anniversary celebration with guided tours, local makers, and live music, 11 a.m. to 3 p.m.), the Twin Star Orchards Mother's Day Market in New Paltz on May 9 and 10 (artisan gifts, wood-fired pizza, hard cider), Mother's Day prix-fixe brunch at the River Pavilion at Hutton Brickyards in Kingston, and scenic train rides on the Catskill Mountain Railroad departing Kingston at 11 a.m., 1 p.m., and 3 p.m.
Is the Catskills Cider Fest family-friendly?
Catskills Cider Fest at Seminary Hill Orchard and Cidery in Callicoon is hosted on a working orchard, so the setting is open and family-friendly during daytime hours, but the focus is hard cider tasting. Confirm age policy and ticket details with Seminary Hill before bringing kids.
Do I need reservations for Mother's Day brunch in the Hudson Valley?
Yes. Mother's Day is one of the busiest restaurant days of the year in the Hudson Valley. Pennings Vineyard, Winding Hills, The Stagecoach Inn, Villa Venezia, and Hutton Brickyards all book out early. Call the venue directly or check their website to reserve.
Which towns does the Caplicki Home Team cover in the Hudson Valley?
The Caplicki Home Team is based in Middletown, NY and serves all of Orange County (every zip code, from Warwick and Goshen to Newburgh, Cornwall, Monroe, Chester, Washingtonville, Pine Bush, Port Jervis, and beyond), plus Sullivan County, Ulster County, and the broader Hudson Valley.
The Caplicki Home Team is a Keller Williams HVU real estate team based in Middletown, NY, serving Orange County, Sullivan County, Ulster County, and the broader Hudson Valley. Reach us at 845-656-4498 or brian@caplickihometeam.com.
