2026 Editor’s Picks: What to Do in the Hudson Valley on May 1 – May 3

The Hudson Valley moves through a full spring weekend of community, creativity and connection—where towns come alive with markets, music, trails and gatherings that bring people together, with the Apple Blossom Festival offering a meaningful moment of support for local farms and growers. #HotList below…

🗓️ WHOLE WEEKEND

🚗 Rhinebeck, Sat May 2 + Sun May 3. Antique Car Show & Swap Meet at Dutchess County Fairgrounds.
A massive showcase of vintage, custom, and classic cars alongside a bustling swap meet filled with auto finds and collector treasures. 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 1

🛍️ Catskill, 9am – 8pm. Catskill First Fridays.
An all-day community celebration with extended shop hours, pop-ups, music, specials, and plenty of sips and snacks throughout town. Info HERE.

🖼️ Athens, 5pm – 7pm. First Fridays at Athens Cultural Center.
An opening reception for a heartfelt student exhibition showcasing young artists’ work across mediums, celebrating creativity, community, and self-expression. Info HERE.

💫 Middletown, 7pm. Star Wars Trivia Night at Clemson Brewing Co.
A high-energy trivia showdown covering Episodes 1–9, deep cuts, and lore with cold beers, bragging rights, and team competition. Info HERE.

🗓️ Saturday, May 2

🏃 Red Hook, 9am – 12pm. A Run to Remember 5K/10K at Greig Farm Trails.
A community run and walk through scenic farm trails honoring loved ones, with a supportive and uplifting atmosphere. Info HERE.

🛠️ Woodstock, 10am – 2pm. Repair Cafe at Woodstock Community Center.
Bring a beloved item for repair and a volunteer will fix it for free while you relax, mingle + chat with your neighbors. Info HERE.

🧀 Washingtonville, 1pm – 5pm. Hudson Valley Mac & Cheese Festival at Brotherhood Winery.
A crowd-favorite food fest featuring creative mac and cheese from top vendors, live music, and a lively, rock-fueled atmosphere. Info HERE.

🏇 Staatsburg, 2pm – 8pm. Kentucky Derby Celebration at Milea Estate Vineyard.
A festive afternoon of Derby Day flair with a special menu, craft cocktails, live music, and statement hat style. Info HERE.

🧺 Gardiner, 2pm. Weaving Wild Baskets Book Launch Party at Full Circle Commons.
A cozy, hands-on celebration with cordage making, storytelling, a reading, and a chance to meet the author and explore handmade basketry. Info HERE.

🌮 Kingston, 4pm. Cinco de Mayo Celebration at Kingston Standard.
A festive hang with tacos hot off the trompo, cold cerveza, and a lively, come-as-you-are crowd. Info HERE.

🍸 Kingston, 4pm – 7pm. Speakeasy Opening Reception at Utopia.
A lively cocktail-driven opening curated by Luke Whittaker, where six painters are paired with drinks for a multi-sensory art experience. Info HERE.

🎸 Woodstock, 7pm. The Pink Floyd Project at Colony Woodstock.
A nine-piece live band delivers an immersive night of Pink Floyd classics with full sound effects and a dynamic light show. Info HERE.

🎧 Catskill, 8pm. AURA Dance Party at The Avalon Lounge.
A late-night dance floor of house, techno, and trance with guest DJs, vinyl sets, and high-energy club vibes. Info HERE.

🗓️ Sunday, May 3

🐦 New Paltz, 7am – 12pm. Spring Migration at Nyquist-Harcourt Wildlife Sanctuary.
An early morning birding walk through forest and wetland trails to spot migrating species in a peaceful natural setting. Info HERE.

🦉 Kingston, 10am – 3pm. Red Owl Flea Season Opening at Red Owl Collective.
A vibrant outdoor flea market packed with antiques, vintage, handmade goods, art, and one-of-a-kind finds from local vendors. Info HERE.

🌸 Hopewell Junction, 11am – 3pm. Apple Blossom Festival & Vendor Market at Fishkill Farms.
A spring-filled day with local vendors, live music, farm eats, wagon rides, and family-friendly activities in the orchard. Info HERE.

💐 Tivoli, 12pm – 5pm. Spring Market at Lasting Joy Brewery.
A lively, rain-or-shine market featuring vintage finds, handmade goods, local vendors, and an all-vinyl DJ set. Info HERE.

🏛️ Kingston, 3pm – 5:30pm. Illuminating Istanbul Lecture at Masa Midtown.
An engaging afternoon lecture exploring Istanbul’s Greek, Roman, and Byzantine history with art, storytelling, and light refreshments. Info HERE.

🌌 Kingston, 3pm. Star Wars Day at Lone Wolf.
A themed celebration with a bespoke menu, raffle prizes, and plenty of galactic fun for fans. Info HERE.

🤖 Woodstock, 3pm. Mario the Maker Magician at Woodstock Playhouse.
A high-energy, all-ages theater show blending robots, magic, and slapstick with interactive moments and big laughs. Info HERE.

Photo of Katterskill Falls by Sharan Singh

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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!