Nestled in the Green Mountains, Wilmington and West Dover offer that classic Vermont blend of cozy village life, rolling landscapes, and unforgettable food. Whether you’re planning a ski weekend, a fall foliage escape, or a quiet mountain retreat, this 3-day itinerary will help you experience the best of southern Vermont — from farm-to-table dining to lakeside strolls and hidden trails.
🌲 Day 1: Arrival, Local Flavor & Fireside Evenings
☀️ Morning: Settle Into Mountain Life
Start your trip by checking into your vacation rental or inn and taking a walk to breathe in that crisp mountain air. The Dover area is dotted with scenic backroads and forested trails perfect for shaking off travel fatigue.
If you arrive early, stop by The Village Roost Café & Marketplace in downtown Wilmington for a strong maple latte and a breakfast sandwich made with local eggs — it’s a cheerful, locals’ favorite start to the day.
🥗 Afternoon: A Taste of Vermont
Spend the afternoon exploring Route 100, the scenic artery that connects Wilmington and West Dover. Pop into Bartleby’s Books or 1A Coffee Roasters, then head to Sawmill Bar & Table for a late lunch or early dinner. Their locally inspired menu — think maple-roasted Brussels sprouts, steak frites, and seasonal soups — captures Vermont’s cozy autumn palette perfectly.
If you’d rather unwind in nature, head up to Hogback Mountain Overlook, where you can see all the way to New Hampshire on a clear day. Just next door, Vermont Distillers offers small-batch tastings of maple bourbon and apple liqueur — the perfect way to toast your first night in town.
🔥 Evening: Settle in by the Fire
After dinner, cozy up back at your lodging. Many local rentals and inns feature fireplaces or outdoor fire pits — ideal for a glass of wine or hot cider under the stars.
🏔️ Day 2: Adventure & Artisanal Eats
🥞 Morning: Classic Vermont Breakfast
Begin with breakfast at Dot’s Restaurant in Wilmington, a local institution for decades and one of the best spots for pancakes and real Vermont maple syrup.
Then, depending on the season:
- Winter: Hit the slopes at Mount Snow, just minutes up the road, known for its diverse terrain and excellent snowmaking.
- Spring/Fall: Head to Molly Stark State Park for a short hike to the fire tower, where 360° views of the Green Mountains reward your climb.
- Summer: Take a paddleboard or kayak out on Lake Whitingham — the largest lake entirely within Vermont — or pack a picnic for Lake Raponda, a peaceful local favorite.
🍽️ Afternoon: Refuel & Stroll
After your outdoor adventure, stop at Two Tannery Road for a hearty late lunch — their burgers and house-made soups hit the spot after time on the trails.
Spend your afternoon exploring Historic Wilmington Village, browsing its art galleries, general stores, and vintage finds. The town’s 19th-century buildings give it a timeless, postcard charm.
🍷 Evening: Farm-to-Table Dining
Dinner is best enjoyed slowly in this part of Vermont. Book a table at The Hermitage Inn, where refined New England cuisine is served beside a crackling hearth. Their wine list and service are top-notch, and the mountain setting is pure serenity.
Prefer something livelier? Head to Trail 87 in West Dover for craft cocktails, wood-fired pizzas, and local art on the walls — a perfect mix of Vermont comfort and creativity.
🚴 Day 3: Small-Town Charm & Slow Farewell
☕ Morning: Local Markets & Morning Light
Ease into your last day with coffee and pastries at Sticky Fingers Bakery — come early for croissants and cinnamon rolls fresh from the oven.
Before you head out, stop at Farmhouse Market or River Valley Market in Wilmington to pick up Vermont cheese, maple syrup, and other local goods to take home.
🚗 Afternoon: Scenic Drive or Leisurely Walk
If you have time, take a scenic detour along the Molly Stark Byway (Route 9) — one of Vermont’s most picturesque drives, connecting Wilmington to Brattleboro with rolling hills, covered bridges, and panoramic overlooks.
Prefer to linger locally? Take one more peaceful walk near your lodging or grab a light lunch at The Social in West Dover, where locally sourced ingredients meet casual, creative cooking in a stylish setting.
Then hit the road — refreshed, full, and ready to plan your next Vermont visit.
🌟 Insider Tips
✅ Book dinner reservations during ski season weekends — tables fill up fast.
✅ Dress in layers — Vermont weather can change from sunny to snowy in a few hours.
✅ Visit in late October or early December for quieter trails and off-peak lodging rates.
🏔️ Why Visit Wilmington & West Dover
Together, these neighboring towns capture the soul of southern Vermont: small-town charm, mountain adventure, and a thriving food scene anchored by local ingredients. Whether you’re chasing snowflakes or sunsets, this is the kind of place that invites you to slow down, savor, and stay awhile.
