2026 Editor’s Picks: What to Do in the Hudson Valley on May 8 – May 10

Mother’s Day weekend in the Hudson Valley is all about slowing down to celebrate Mom at markets, music, brunches, orchard hangs, art, nature + meaningful community moments. Hot List below…

🗓️ ALL WEEKEND

🛍️ Hudson, Sat May 9 + Sun May 10, 10am – 5pm. Basilica Farm & Flea Spring Market.
A weekend-long gathering of makers, vintage finds, farm goods, workshops, live performances, and hands-on family activities celebrating spring, creativity, and community. Info HERE.

🍏 Marlboro, Sat May 9 + Sun May 10, 11am – 5pm. Mother’s Day Weekend Celebration at Weed Family Orchards & Winery.
A relaxed weekend outing with wine, food trucks, and a laid-back atmosphere designed for celebrating and spending time with Mom. Info HERE.

🥬 Hudson Valley, All weekend! Your Ultimate Guide to the Hudson Valley’s Vibrant Farmers Markets: Spring to Fall.
Your go-to guide to the Hudson Valley’s vibrant Farmers Markets, spring through fall—where fresh seasonal produce, local farms and community come together. Info HERE.

🗓️ Friday, May 8

🎞️ Marlboro, 11am – 1pm. Composition in the Field at Gomez Mill House.
A guided, hands-on photography session blending instruction and a scenic walk through historic grounds to sharpen composition skills and capture striking images. Info HERE.

🥾 Arkville, 2pm – 4pm. CFA Speaker Series: Packed for Adventure – Hiking in the 1800’s at Catskill Forest Association.
A multimedia presentation exploring historic hiking gear, food, and clothing in the Catskills, with stories and anecdotes from John Burroughs and others. Info HERE.

🎶 Woodstock, 7:30pm – 9:30pm. Live Dinner Show: Brad Cole & Bossa Blue at Pearl Moon.
An intimate, high-energy dinner show blending blues, soul + global grooves with dynamic live musicianship in a warm, immersive setting. Read the interview with Brad Cole. Info HERE.

🗓️ Saturday, May 9

🎶 Saugerties, 11am – 3pm. Community Day at Opus 40.
A family-friendly celebration with live music, hands-on crafts, free tours, and local makers set among the iconic stone sculpture park. Info HERE.

🖌️ Poughkeepsie, 11am – 4pm. Kinusaiga Textile Art Workshop.
A beginner-friendly hands-on workshop exploring Japanese fabric art techniques to create a stitched-free textile “painting” perfect for gifting or display. Info HERE.

🍄‍🟫 Hudson, 12pm – 4pm. Forage Fest at Creative Legion.
A celebration of wild, seasonal, and local food featuring chef-driven tastings, foraged cocktails, a maker market, inspiring talks, and guided foraging experiences. Info HERE.

🎧 Round Top, 12pm – 8pm. Opening Weekend DJ Sets at Glen Falls House.
A lively kickoff to the season with stacked DJ sets, food trucks, and a festive outdoor spring atmosphere. Info HERE.

🌎 Kingston, 1pm. Kingston Earth Fair at TR Gallo Park.
A lively waterfront celebration with live music, food trucks, local vendors, eco exhibits, kids activities, and community-focused fun. Info HERE.

🪴 Poughkeepsie, 1pm – 5pm. A Mid Hudson Expo: Plantella at MJN Convention Center.
high-energy plant experience bringing collectors and beginners together with vendors, community, and a lively marketplace atmosphere centered around discovery and connection. Info HERE.

🪑 Port Ewen, 1pm – 5pm. The Big Tent Designer + Decorator Sale at Ball & Claw Antiques.
A special pop-up sale featuring curated furniture, art, lighting, tabletop pieces, and styling finds from top designers + antique dealers. Info HERE.

🍎 Callicoon, 1pm – 9pm. 2nd Annual Catskills Cider Festival at Seminary Hill.
A celebratory afternoon of regional cider pours from top producers, followed by a curated cider-paired dinner with live jazz and seasonal Hudson Valley flavors. Info HERE.

🍏 Stone Ridge, 2pm til late. 30th Annual Spring Wassail at Stone Ridge Orchard.
A lively celebration of spring with traditional folk dancing, live Balkan music, and a communal ritual honoring the season’s return and harvest to come. Info HERE.

👩‍🎨 Woodstock, 2pm – 4pm. “This is America” Artist Talk: Lindsey Guile at Woodstock School of Art.
thought-provoking artist talk series exploring how cultural and ancestral histories shape artistic practice through storytelling, perspective, and dialogue. Info HERE.

🗓️ Sunday, May 10

🌺 East Windham, 11am – 3pm. Mother’s Day Social at Dandies.
A relaxed glasshouse + biergarten hang with brunch specials, cocktails for moms, and pup-friendly treats in a laid-back mountain setting. Info HERE.

🥂 New Paltz, 11am – 3pm. Mother’s Day Brunch at Pitanga North.
A three-course prix fixe brunch with a complimentary mimosa for moms, plus dinner service and patio seating for a full day of celebration. Info HERE.

🌷 New Paltz, 11:30am – 2:30pm. Mother’s Day Grand Buffet at Mohonk Mountain House.
A full day celebration with a spring buffet, tulip garden tours, spa time, scenic trails, and festive touches like mimosas, photo moments, and a complimentary champagne cocktail for Mom. Info HERE.

👒 Woodstock, 6:30pm – 9:30pm. Mother’s Day Dinner Show at Colony Woodstock.
An intimate evening of live music paired with dinner and drink specials in a relaxed, celebratory setting. Info HERE.

Photo of and by Opus 40 in Saugerties NY—created by Harvey Fite over four decades, this 6.5-acre bluestone earthwork rises from an abandoned quarry at the base of Overlook Mountain and, since opening to the public in 1978, continues as a living artwork and cultural space hosting tours, events, and performances shaped by the surrounding landscape.

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Be sure to visit our Event Calendar HERE for more amazing happenings in the Hudson Valley.

Have a wonderful weekend from Inside+Out Upstate NY!