Weekend Itinerary
Friday afternoon
Check into one of our four inns located right in downtown, each offering a unique experience. The Wilmington Inn provides a cozy, country inn feel with attentive owners who make you feel at home. The Vermont House is perfect if you’re looking to stay in a historic building with a touch of independence. The Crafts Inn features a relaxing pool and spa, while Valley Craft Ales offers live music and a brewpub inside, making it an ideal spot for craft beer enthusiasts.
Friday night
Make a dinner reservation at Alpenglow to taste your way through the Alps, indulging in rich flavors traditional dishes inspired by the region’s culinary heritage. Experience the warmth of Alpine hospitality in a cozy, mountain-inspired setting.
Friday late night
Head down to the Wilmington Village Pub, open for over 30 years, where you’ll find friendly faces, lively conversations, and spirited karaoke night! Enjoy a cold pint and soak in the welcoming atmosphere that keeps people coming back.
saturday morning
Grab breakfast at Dot’s, the longest-standing restaurant in downtown, where you can enjoy delicious homemade classics, friendly service, and a warm, welcoming atmosphere that has been a local favorite for generations.
saturday midday
Head over to Pettee Memorial Library to rent a pair of snowshoes and enjoy a leisurely hike down the Hoot Toot & Whistle! A beautiful and peaceful way to immerse yourself in nature.
saturday midday
Stroll through downtown, soaking in the charming atmosphere while popping in and out of our many unique shops, where you’ll find everything from locally crafted goods, artisan gifts and specialty boutiques.
saturday afternoon
Enjoy lunch at 19 South Main alongside a life-sized Bob Ross cutout! Relax in the rustic-modern ambiance while savoring wood-fired pizzas, flavorful pastas, and fresh salads. With a full bar and a creative and varied menu, it’s the perfect spot for a delicious and memorable dining experience.
saturday Evening
Schedule a creative art class taught by talented local artists, where you can unleash your creativity, and take home a unique piece of artwork as a special souvenir.
saturday night
Grab dinner at The Anchor, a beloved staple that has been serving up delicious seafood in the heart of the Green Mountains for 25 years. Enjoy fresh catches, hearty New-England spired dishes, and a cozy, welcoming atmosphere that makes every meal feel like a special occasion.
Sunday morning
Grab a coffee and pastries at The Village Roost and cozy up in front of the fire. Let the charming, rustic setting make you feel right at home as you unwind and savor every bite.
Sunday midday
Grab a pamphlet from the Visitors Center and follow along with our historic walking tour. Learn about the rich history of our downtown, explore historic photos, and compare them to how the buildings look today.
Sunday afternoon
Be sure to hit the Maple Leaf Tavern for lunch on your way out of town. Enjoy a laid back setting before you hit the road.