Spend your holiday weekend in Southwestern Vermont, where the mountains meet charming villages filled with unique shops, cozy restaurants, and winter fun. From skiing down Stratton Mountain’s powdery slopes to discovering one-of-a-kind gifts in eclectic shops, here's a guide to an unforgettable weekend in The Shires!
Day 1: Arrival & Warm Welcome
Check-in at the Equinox Golf Resort & Spa
Kick off your stay in style at the historic Equinox Resort. Nestled in the heart of Manchester, this luxurious escape offers cozy rooms, beautiful grounds, and a soothing spa to unwind after your journey.
Evening Dinner at Silver Fork
For an intimate dining experience, book a table at Silver Fork, known for its world-inspired menu and use of local ingredients. Enjoy dishes that bring together Vermont’s unique flavors with international flair, perfect for setting a festive tone to your weekend.
Day 2: Snow Adventures & Local Shopping
Morning Ski or Snowboard at Stratton Mountain
Rise early for a day on Stratton Mountain’s picturesque slopes! With runs for every skill level, Stratton provides an incredible skiing or snowboarding experience. The resort also has rentals and classes for beginners, so everyone can enjoy the snow.
Afternoon Shopping Spree
After your morning adventure, explore some of Southwestern Vermont's most charming shops to find unique gifts for everyone on your list.
Northshire Bookstore (Manchester)
A literary haven, Northshire Bookstore offers an extensive selection of books, games, and gifts for all ages. Discover Vermont authors, browse cozy reads, or pick up unique souvenirs in their curated gift section.Vermont Flannel Co. (Manchester)
Stop by Vermont Flannel’s flagship store to pick up some of the softest, coziest flannel apparel around. It’s a wonderful Vermont keepsake or gift to keep loved ones warm this winter.Lapeche
Discover high-quality women's fashion and accessories at Lapeche. This stylish boutique offers a carefully curated selection, perfect for holiday gift shopping or a festive treat for yourself.HN Williams Store (Dorset)
With over 175 years of history, HN Williams Store is a quintessential Vermont experience. From cozy flannel shirts to locally-made snacks, this store captures the heart of New England.Rablogon Castle (Arlington)
Step into a world of medieval charm at Rablogon Castle, where you’ll find unusual treasures, antiques, and artifacts. It's a destination in itself and a perfect stop for those with a taste for the extraordinary.
Sweet Treats and Antiquing (Bennington)
A trip to Bennington, 30 minutes south of your room, wouldn’t be complete without some sweet treats and a little treasure hunting. Start with a visit to the Village Chocolate Shoppe, where you can indulge in hand-crafted chocolates, truffles, and holiday-themed sweets. Their Vermont Maple Creams and specialty chocolates make for delightful gifts or an indulgent treat for yourself.
After satisfying your sweet tooth, spend some time exploring the antique shops in Bennington, where you’ll discover a variety of vintage furniture, collectibles, and unique items that capture the charm of Vermont’s past.
Dinner at Union South (Bennington)
End the day with a meal at Union South, Bennington’s newest restaurant and bar located in the historic Putnam Block building. With a locally sourced menu, craft cocktails, and an entertainment venue, Union South offers a vibrant dining experience.Day 3: Relaxation & Exploring the Shires
Day 3: Rest, Relax & Repeat
Morning Spa Session at the Equinox Spa
Treat yourself to a luxurious morning at the Equinox Spa. Their skilled therapists offer everything from deep tissue massages to revitalizing facials, perfect for easing any post-skiing soreness.
Lunch at CurATE
For lunch, visit CurATE at SVAC, where art and cuisine come together beautifully. This intimate, art-inspired café offers a menu that highlights local, seasonal ingredients with a creative twist. The dishes are as visually appealing as they are delicious, making for a unique dining experience surrounded by the arts.
Afternoon at the Southern Vermont Arts Center (SVAC)
After an active morning, spend the afternoon immersed in art at the Southern Vermont Arts Center in Manchester. SVAC features diverse galleries with rotating exhibits, showcasing works by both local and national artists. Stroll through the sculpture garden, explore the indoor galleries, and take in the beautiful blend of art and nature.
Evening Dinner at The Dorset Inn
Conclude your day with a fine dining experience at The Dorset Inn, Vermont's oldest continuously operating inn. The inn’s charming, historic ambiance paired with a seasonal menu offers a delightful dining experience you won’t forget.
Day 4: Farewell Brunch & Last-Minute Finds
Brunch at Ye Olde Tavern (Manchester)
Before heading home, enjoy a delicious farewell brunch at Ye Olde Tavern, a historic gem in Manchester. Their Vermont-inspired brunch menu will send you off with warm memories and perhaps a few maple-flavored treats.
Quick Stop at Woodford Mountain General Store
For a final touch of Vermont, stop by this local favorite for unique snacks, gifts, and last-minute finds that capture the essence of your holiday in the Shires.
This holiday long weekend itinerary is your gateway to a blend of adventure, relaxation, and local charm. With stunning scenery, one-of-a-kind shops, and experiences designed to make memories, Southwestern Vermont is the perfect destination for your next holiday getaway. Happy exploring!