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
Reserve a table 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's you enjoy dinner on the deck under the bistro lights.
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
Start your midday adventure by crossing Reardon Bridge and setting out on the Hoot Toot & Whistle Trail, a scenic 3.8 mile out-and-back hike. Follow the trails to the shores of Lake Whitingham, where you can cool off with a refreshing swim before making your way back to town.
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
Soak up the sunny vibes with lunch on the deck at The Anchor, a local favorite that's been serving up fresh seafood and hearty New-England inspired dishes for over 25 years,. It's the perfect spot to savor summer flavors and soak up the. lively downtown energy!
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
Spend a perfect summer evening at Valley Craft Ales on Jerry's Deck, a beloved downtown hangout for generations. Kick back with a fresh piping hot pizza, sip on VCA's signature brews, and soak up the sounds of live music under the evening sky.
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
Start your morning at our newly renovated Charles Trebbe Jr. Tennis and Pickleball Courts! Borrow rackets and balls from Pettee Memorial Library, and don't forget to enjoy a quick game go ping pong at the table just outside the courts!