The Perfect Thanksgiving Weekend in the Hudson Valley
Nestled in the heart of the Hudson Valley, Red Cottage offers the perfect blend of cozy comfort and adventure: the ease of a home-style base, the charm of rural escape, and access to gorgeous scenery, local food, and seasonal events. Spend less time worrying about logistics and more time enjoying what matters: family, friends, gratitude and a little fun.
Wednesday: Arrival & Settling In
Settle into your Red Cottage rental and soak up the quiet before the holiday bustle begins. Once you’ve unpacked, head into town to stock up on local favorites for your feast.
Stop and pick up pies for the big day. We recommend Bread Alone Bakery in Woodstock for their classic apple pie, Montgomery Place Orchards in Red Hook for a crumb-topped fruit pie made with their own produce, or Rosie’s General in Kingston for a little bit of everything, pies, baguettes, bagels and any other last minute groceries. Most spots take preorders, so check ahead for hours.
After your pie run, enjoy a casual dinner in town. Grab wood-fired pizza and a local cider at Twin Star Orchard’s in New Paltz or tuck into comforting seasonal dishes at SILVIA in Woodstock. End the evening back at your cottage with a fire and a glass of wine or hot cider to toast the weekend ahead.
Thursday: Turkey Trot + Thanksgiving Feast
Kick off Thanksgiving morning with the Woodstock Turkey Trot, a fun 5K run and walk that starts right in the village center. Afterward, refuel with breakfast at Pearl Moon or Moonrise Bagels, both local favorites for hearty morning plates, fun bagels and great coffee.
Spend the afternoon at the cottage cooking your feast or relaxing by the fire while the kitchen fills with all the best smells of the season. When it’s time for dessert, you’ll be glad you picked up those local pies.
If you’re looking to stretch your legs later in the day, take a drive through Overlook Mountain Trailhead or stroll the Ashokan Rail Trail, where the late-autumn light over the reservoir is picture-perfect. End the evening cozy inside, playing board games or watching a movie with leftover pie.
Friday: Farm Stands + Small-Town Shopping
Sleep in a bit, then head out for brunch at Cafe Mutton in Hudson or Gracie’s Luncheonette in Leeds, both known for locally sourced menus that highlight Hudson Valley farms.
After brunch, explore the area’s best farm stands. Wallkill View Farm Market in New Paltz has incredible local produce and baked goods, while DuBois Farms in Highland offers a market, hard cider tasting, and scenic views. Stop for some fresh-pressed cider, local cheese, and jams to bring back to your cottage.
Spend the afternoon wandering through charming downtowns like Rhinebeck, Hudson, or Phoenicia, browsing artisan shops and early holiday markets. For dinner, make a reservation at Miss Lucy’s Kitchen in Saugerties or enjoy a big dry aged steak at The Phoenician Steakhouse.
Saturday: Scenic Sips + Cozy Evenings
Start your day with a light breakfast at the cottage or pastries from Shandaken Bake, then head out for a short hike or scenic drive. Try Minnewaska State Park Preserve near New Paltz for breathtaking overlooks or Poets’ Walk Park in Red Hook for an easy trail with views of the Hudson River.
In the afternoon, it’s time for some local sipping. Stop by Klocke Estate in Hudson for brandy and sweet vermouth made on-site, or visit Westwind Orchard in Accord for wood-fired pizza and organic hard cider in a rustic-chic setting. If you’re more into beer, Arrowood Farms in Accord brews excellent farmhouse-style ales and often hosts live music on weekends.
Back at your cottage, cook a relaxed group dinner or enjoy leftovers by the fire. End the evening stargazing on the deck or playing cards indoors while the night settles around you.
Sunday: Slow Morning + Farewell
Take your time on Sunday morning with one last breakfast together. If you’re heading south, stop at Village Coffee and Goods in Kingston or Josie’s Coffee Shoppe in Saugerties for a cozy sendoff.
Before you hit the road, pop into a local farm stand like Greig Farm in Red Hook to pick up maple syrup, local honey, or jam as souvenirs from your Hudson Valley Thanksgiving weekend.
A Thanksgiving to Remember
Whether you’re running the Woodstock Turkey Trot, tasting cider at Westwind Orchard, or just relaxing fireside at your Red Cottage stay, Thanksgiving in the Hudson Valley is pure magic. With farm-fresh food, cozy small towns, and beautiful scenery at every turn, it’s the perfect mix of celebration and calm before the holiday season begins.
