As fall settles in, bringing crisp air and a kaleidoscope of colors, it’s the perfect time for a laid-back getaway. In Hudson Valley, NY, you can enjoy cozy layers and comfy ankle boots while exploring local vineyards and charming towns bursting with autumn vibes. Woodstock offers a relaxed, artsy atmosphere where flannel shirts and well-loved jeans are perfect for hiking and discovering quirky shops. Over in Stowe, Vermont, wrap yourself in a soft sweater and take in the stunning mountain views while sipping hot cider amidst the fall foliage. Charlottesville, VA, is a delightful blend of history and wine country, inviting you to enjoy vineyard picnics in casual attire as you soak up the scenery. Lastly, Jackson, Wyoming, calls for a rugged yet relaxed look for outdoor adventures, with evenings spent around a cozy fire. Each of these destinations offers a wonderful escape, perfect for enjoying the simple pleasures of the season. Keep scrolling for all the recommendations on where to stay, where to eat, and what to explore.
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Fall Travel Inspiration
WOODSTOCK, VERMONT
WOODSTOCK Recommendations
Woodstock Inn & Resort – A quintessential New England retreat, this charming inn offers cozy rooms, an inviting fireplace, and easy access to nature walks to enjoy the fall foliage.
The Prince & The Pauper – A fine dining restaurant with a warm, rustic ambiance, perfect for a special meal.
Worthy Kitchen – A farm-to-table eatery serving craft beer and delicious comfort food like burgers and local produce.
F.H. Gillingham & Sons – A historic general store where you can shop for unique home goods, Vermont-made products, and specialty foods.
The Art of Craft – A boutique featuring artisan home décor, handcrafted jewelry, and clothing with a focus on local craftsmanship.
Billings Farm & Museum – Take in the pastoral beauty of Vermont’s farmland and learn about the area’s history.
Marsh-Billings-Rockefeller National Historical Park – Stroll through beautiful trails surrounded by vibrant foliage.
CHARLOTTESVILLE, VIRGINIA
CHARLOTTESVILLE Recommendations
Charlottesville, Virginia, is a vibrant city steeped in history and culture, best known as the home of Thomas Jefferson and the University of Virginia. With its stunning mountain backdrop and historic charm, Charlottesville offers a delightful mix of attractions, from the iconic Monticello to lively downtown shops and restaurants. Visitors can explore the picturesque parks, enjoy local wineries, and immerse themselves in the region’s rich arts scene. With its blend of Southern hospitality and academic energy, Charlottesville is an inviting destination for history buffs, outdoor enthusiasts, and food lovers alike.
Keswick Hall – Stay at this historic luxury resort is nestled in the rolling hills of Virginia’s wine country, offering elegant accommodations, beautiful views of the countryside, and cozy fireplaces for those chilly fall nights.
The Ivy Inn – A charming, upscale restaurant located in a historic house, serving farm-to-table dishes that highlight local Virginia ingredients.
Tavola – A cozy, intimate Italian restaurant in Belmont, perfect for a comforting pasta dish paired with excellent wine.
Caspari – A delightful boutique offering beautiful home décor, tabletop items, and unique gifts perfect for fall entertaining.
Scarpa – A chic women’s boutique offering high-end clothing, shoes, and accessories, with an emphasis on stylish yet timeless pieces.
Quirk Gallery – Located in downtown Charlottesville, this boutique art gallery and shop features home goods, accessories, and art pieces from local and regional artists.
Monticello – Visit Thomas Jefferson’s historic home surrounded by vibrant fall foliage. The gardens and views from the estate are particularly stunning in autumn.
Carter Mountain Orchard – Take in sweeping views of the Blue Ridge Mountains while apple picking or enjoying seasonal cider donuts. This spot is especially magical for watching the leaves change.
Virginia Wine Trail – Charlottesville is located in the heart of Virginia’s wine country. Spend a day exploring nearby vineyards like King Family Vineyards or Barboursville Vineyards, known for their excellent wines and scenic settings.
HUDSON VALLEY, NEW YORK
HUDSON VALLEY Recommendations
The Hudson Valley, New York, is a dynamic region celebrated for its breathtaking river views, vibrant communities, and rich agricultural heritage. This area is a haven for outdoor lovers, featuring hiking trails in the Catskills, serene riverside parks, and numerous orchards and farms. The Hudson Valley is also a cultural hotspot, home to a variety of art galleries, music festivals, and historic sites, including grand estates and charming historic towns. With its diverse culinary scene, including artisanal markets and farm-to-table restaurants, the Hudson Valley invites visitors to savor local flavors while enjoying a relaxed, scenic atmosphere.
Troutbeck – Nestled in the Hudson Valley, this luxurious estate hotel offers an intimate, cozy ambiance with plush accommodations, perfect for relaxing after a day of leaf-peeping.
Swoon Kitchenbar – A Hudson hotspot serving inventive farm-to-table dishes in a chic, relaxed setting.
Hawkins New York – A boutique offering chic, modern home goods and design-forward décor items.
Lili and Loo – A lifestyle shop in Hudson featuring global home décor, jewelry, and eclectic clothing..
Olana State Historic Site – Explore the historic home of artist Frederic Edwin Church and enjoy sweeping views of the Hudson River Valley.
Storm King Art Center – An open-air museum featuring large-scale sculptures set amidst the beautiful fall landscape.
STOWE, VERMONT
STOWE Recommendations
Stowe, Vermont, is a charming alpine town known for its breathtaking mountain scenery and outdoor adventures. Often referred to as the “Ski Capital of the East,” Stowe attracts winter sports enthusiasts with its world-class slopes and cozy après-ski atmosphere. In the warmer months, the area transforms into a hiker’s paradise, featuring lush trails and stunning views. The town itself boasts a delightful mix of quaint shops, art galleries, and farm-to-table dining options, offering visitors a taste of local culture and cuisine. With its enchanting landscape and vibrant community, Stowe is the perfect destination for both adventure seekers and those looking to relax in a serene setting.
Topnotch Resort – This luxurious yet rustic resort offers a warm and welcoming atmosphere with cozy accommodations, a world-class spa, and stunning views of Mount Mansfield.
The Whip Bar & Grill – Enjoy New England classics with locally sourced ingredients in a cozy, casual setting.
Doc Ponds – A relaxed spot with craft beer and comfort food, perfect for a laid-back evening.
Stowe Craft Gallery – A shop featuring handmade jewelry, home décor, and gifts crafted by local artisans.
Coco Goose – A women’s boutique that carries high-end clothing and accessories from designer brands.
Stowe Pinnacle Trail – For the adventurous, this hike offers stunning panoramic views of the autumn landscape.
Smugglers’ Notch – Drive or hike through the notch to see incredible fall foliage, rocky cliffs, and scenic vistas.
JACKSON, WYOMING
JACKSON Recommendations
Jackson, Wyoming, is a stunning gateway to the American West, nestled in the shadow of the majestic Teton Range. Known for its breathtaking natural beauty and vibrant outdoor lifestyle, Jackson is a hub for skiing, hiking, and wildlife viewing. The town’s lively square is filled with charming shops, art galleries, and renowned restaurants, showcasing the region’s rich culture and culinary scene. Visitors can explore nearby Grand Teton and Yellowstone National Parks, making it an ideal base for adventure seekers. With its blend of rugged wilderness and Western charm, Jackson offers a unique and unforgettable experience for all who visit.
Amangani – A luxury mountain resort with breathtaking views of the Grand Tetons, cozy fireside lounges, and ultimate seclusion. Perfect for a serene fall escape.
Snake River Grill – A Jackson favorite with a rustic-chic vibe serving elevated comfort food and local game.
The Kitchen – Modern American cuisine with a focus on seasonal ingredients and an intimate, cozy atmosphere.
MADE – A boutique featuring unique, handcrafted home goods and gifts made by local artisans.
Mountain Dandy – A carefully curated shop offering beautiful home accessories and gifts with a rustic, Western flair.
Altamira Fine Art – A gallery showcasing stunning works of Western art, perfect for adding a bit of Jackson Hole’s rustic charm to your home.
Grand Teton National Park – Take in the majestic views and autumn colors while exploring scenic hiking trails.
National Museum of Wildlife Art – Discover beautiful wildlife-themed art in a setting that overlooks the stunning valley below.