Top Holiday Markets to Visit This Winter in Upstate NY
The Hudson Valley comes alive in winter with festive holiday markets packed with handcrafted gifts, small-batch treats, and one-of-a-kind finds you won’t get anywhere else. Whether you’re hunting for the perfect present or looking to support local artists, makers, and small businesses, these markets make winter shopping feel fun instead of stressful. From cozy indoor fairs to twinkling outdoor pop-ups, consider this your guide to the best holiday markets in the Hudson Valley this season. Don’t rush home and book a Red Cottage stay so you can savor the holiday cheer and market hop all weekend long!
📍Cannonball Factory Market
🗓️ November 28-30 December 5-7, 12-14, 19-21
Step into Hudson’s Cannonball Factory for a weekend of local artisans, handmade goods, and festive finds. From unique gifts to tasty treats, there’s something for everyone on your holiday list. Support small businesses while enjoying a cozy, creative atmosphere.
📍Twin Star Orchard Holiday Market
🗓️ Saturdays November 22– December 20
Stroll through Twin Star Orchard’s winter market, where fresh cider, baked goods, and handcrafted gifts await. It’s the perfect place to cross off your holiday shopping list while enjoying scenic orchard views. Don’t miss the chance to meet local makers in a festive setting.
📍Makers Central Holiday Makers Market
🗓️ December 20-21
Makers Central transforms its shared studio warehouse in Tarrytown into a festive holiday market full of handmade treasures and local talent. Expect a scavenger hunt for kids, a family‑friendly cocktail hour, live music, and brunch specials (mimosas for the first 100 guests). It’s a joyful, community‑driven shopping experience that puts local makers front and center.
📍The Farmhouse Project Holiday Makers Market
🗓️ December 13-14
The Farmhouse Project invites you to its beautifully curated holiday makers market in Callicoon, featuring a thoughtful selection of artisans, designers, and makers. Set in the Delaware Youth Center, it’s a spot to discover heirloom-quality gifts and slow‑made treasures. While shopping, you’re supporting local creatives who bring craftsmanship and care to every piece.
📍Basilica Farm & Flea
🗓️ November 28–30
Hudson’s Basilica Farm & Flea transforms into a holiday wonderland with artisanal gifts, vintage finds, and tasty treats. Discover one-of-a-kind treasures while supporting independent makers and local entrepreneurs. Perfect for a leisurely day of festive shopping.
📍Troutbeck Holiday Bazaar
🗓️ December 6-7
Troutbeck hosts a charming holiday bazaar in Amenia, featuring local artists, craft vendors, and seasonal specialties. Explore unique gifts for everyone on your list while enjoying the historic ambiance. This market is ideal for a relaxed, festive outing.
📍Make Your Mark[et]
🗓️ November 28-December 24
Irvington’s Make Your Mark[et] brings local makers together for a festive day of shopping and community. From handcrafted goods to seasonal treats, it’s a perfect spot for unique holiday gifts. Celebrate the season while supporting Hudson Valley artists.
📍HoliYAY! Market
🗓️ December 13-14
Peekskill’s Yay! Market HoliYAY! Market is full of holiday cheer, handmade gifts, and delicious local goodies. Browse artisan stalls, find one-of-a-kind presents, and enjoy a lively, festive atmosphere. Every purchase helps support small businesses in the Hudson Valley.
📍The Holiday Shoppe by The Floral Society
🗓️ December 14–15
Dobbs Ferry’s Holiday Shoppe is a floral-inspired market featuring handcrafted gifts, seasonal décor, and unique finds. Perfect for last-minute shopping or treating yourself, this market celebrates local creativity. Explore, shop, and support independent makers in a festive setting.
📍Wickers Creek Market, Holiday Edition at HudCo
🗓️ December 13
This vintage + antiques market is moving indoors for the holidays to HudCo at Hudson River Landing in Dobbs Ferry. Think rare collectibles, curated vintage finds, and a handful of makers all under one cozy roof. It’s a perfect stop to score thoughtful, timeless gifts while supporting local curators and artisans.
📍Craft Fest at Stissing House
🗓️ December 13-14
Stissing House hosts its third annual “Craft Feast,” where about 50 makers fill the historic tavern with ceramics, baskets, textiles, knives, and more. You’ll also find live caroling, seasonal broth, and a warm, community‑oriented vibe that feels both timeless and festive.
📍 Bethel Woods Holiday Market
🗓️ November 28–30
Bethel Woods brings back its beloved three-day Holiday Market over Thanksgiving Weekend with more than 75 local artisan and specialty food vendors. This is the perfect place to shop thoughtfully for gifts while supporting regional makers and small businesses.
After a day of exploring the Hudson Valley’s holiday markets, don’t head straight home, extend the festive fun with a cozy Red Cottage stay. Sip hot cocoa, unwrap a little downtime, and let the winter charm soak in while you plan your next market adventure. With so many makers, treats, and twinkling lights to explore, a weekend getaway is the perfect way to make the season feel extra special.
