A Weekend Escape to Wilmington, Vermont ☀️ Summer Edition
- earthboundescapesi
- Aug 15, 2024
- 10 min read
Nestled in the heart of southern Vermont, Wilmington is the perfect weekend escape for those living in NYC and Westchester County. Just a 4-hour drive from the hustle and bustle of the city and a 3-hour drive from the suburbs, this charming town offers a refreshing change of pace without the hassle of long-distance travel. The journey itself is a breeze, especially if you set out early in the morning to beat the traffic.
As someone who spends almost every weekend in Wilmington throughout Summer, Fall, and Winter, I can attest to Wilmington's year-round appeal. This quaint town, full of character and New England charm, transforms with each season, offering visitors a unique experience every time they return. Whether you're seeking outdoor adventures, culinary delights, or simply a peaceful retreat, Wilmington has something for everyone. Let me break down the essentials for your perfect weekend getaway:
Where to Stay:
White House Inn: Perched majestically on a hilltop, The White House Inn offers a picturesque escape steeped in history. Built in 1915, this charming inn has lovingly preserved its quirks and whimsical touches through the decades, offering guests a unique blend of vintage charm and modern comfort. The spacious rooms, most boasting adorable private balconies, provide stunning views over the quaint town below.
Your stay includes a delightful breakfast at Clara's Cucina, the inn's inviting restaurant. For a truly magical experience, grab a cocktail and head to the terrace to watch the sun paint the sky in vibrant hues as it sets over Wilmington. This nightly spectacle is a favorite among guests and a perfect way to unwind after a day of exploration.
The Wilmington Inn: The Wilmington Inn, a jewel of local history, began its story in 1894 as a personal residence. Today, this restored bed and breakfast captures the essence of Vermont hospitality. Cozy, well-appointed rooms invite relaxation, while the outdoor fire pit offers a perfect gathering spot to enjoy local craft beers under the stars.
The inn's gourmet breakfasts are a highlight, featuring locally sourced ingredients that showcase the flavors of Vermont. With its perfect blend of historic charm and modern amenities, The Wilmington Inn provides an intimate, home-away-from-home experience that captures the heart of Wilmington's allure.
Airbnb options: For a more home-like experience, numerous charming cottages and cabins are available. Here are some I recommend:
For Couples Retreats:
For Group Getaways:
Things to Do:
Explore downtown Wilmington's antique shops and boutiques. Stroll through Wilmington's charming downtown area, where you'll find a delightful mix of antique shops and unique boutiques.
Start your morning with a round of golf! Enjoy the scenic beauty of Vermont while perfecting your swing at the Haystack Golf Club or the Mount Snow Golf Club.
Go on a Hike! Lace up your boots and explore the natural beauty of the area. I have listed my favorite hikes below:
Mount Snow Peak- You will start this hike at the mountain base, where a well-maintained trail guides you through a serene forest setting. As you ascend, the dense woods gradually give way to open mountain slopes, providing increasingly breathtaking views of the surrounding Green Mountains. The final stretch presents a more challenging vertical trek, but your efforts are handsomely rewarded upon reaching the Bull Wheel Summit Lodge. Here, you can catch your breath, enjoy a well-deserved beer, and take in the stunning 360-degree panorama of southern Vermont's rolling hills and valleys. While you're up there, make sure to catch a view of Seahorse Lake. The lookout will be on the left-hand side of the summit (if you're looking down slope).
Mt Olga Trail (Map)- Nestled in the heart of Molly Stark State Park, the Mt. Olga Trail offers a perfect blend of natural beauty and local flavor. Begin your adventure at the trailhead, where a modest $5 fee grants you access to this gem of southern Vermont. The trail itself is a moderate 1.8-mile loop that winds through lush forest before culminating at a historic fire tower lookout. This summit holds a special place in my heart as the spot where my husband proposed.
About halfway through the loop, you'll encounter trail signs pointing towards the Hogback Mountain Trailhead and parking lot. Here's where the hike takes an interesting twist: if you follow the signs towards Route 9, you'll find yourself at the doorstep of Vermont Distillers, with Beer Naked Brewery just across the street. At the distillery, you can enjoy fresh cocktails with the locally crafted spirits or craft beers and pizza at the brewery. Both provide gorgeous panoramic views of the state park.
Haystack Mountain Trail (Map)- This 4-mile out-and-back trail offers a perfect blend of accessibility and reward. Moderately challenging yet dog-friendly, it's ideal for families and hikers of various skill levels. The summit rewards with stunning views, making the effort worthwhile. While it can get busy later in the day, an early start ensures a more peaceful experience. With its easy-to-find trailhead and manageable terrain, Haystack Mountain Trail is a go-to option for those seeking a satisfying Vermont hiking adventure without extreme difficulty.
Hamilton Falls Trail (Map)- This 5.8-mile out-and-back gem in Jamaica State Park is well worth the 30-minute drive. Arrive early to fully enjoy the numerous waterfalls and pools that make this hike a refreshing adventure, especially for dogs. The trail offers tranquil forest scenery, but be prepared for potential crowds near Hamilton Falls itself, as there's separate parking access. Despite this, it remains one of Vermont's most rewarding hiking experiences.
Gilbert's Lookout and Owl's Head (Map)- This is a demanding 4-mile out-and-back trail in Dorset, Vermont. While the hour-long drive to the trailhead might deter some, the stunning overlook views and the charming nearby town of Manchester make it a worthwhile adventure. After your hike, treat yourself to a stroll and lunch in Manchester's picturesque downtown, perfectly complementing your outdoor expedition
Windsor Trail (Map)- Nestled in Mt. Ascutney State Park (approximately 1 hour from Wilmington), The Windsor Trail offers a formidable 5.3-mile hiking experience that stands out as one of the more demanding treks in the area. With an impressive elevation gain of 2,500 feet, this trail provides a true test of endurance. The climb is challenging, but the payoff is substantial. Upon reaching the summit, you're greeted with breathtaking panoramic views that stretch across the Vermont countryside. After the hike stop at Harpoon Brewery for lunch and a couple of craft beers.
Spend the afternoon boating on the Harriman Reservoir! Immerse yourself in the natural beauty of Harriman Reservoir, also known as Lake Whitingham. This expansive body of water offers a perfect setting for a variety of water activities. Head to High Country Marine, where you can rent a boat for a leisurely cruise around the lake, or opt for a kayak or paddleboard to explore the shoreline at your own pace. I recommend booking your rentals in advance on their website, when we have nice weather everyone is on the lake!
Brewery Hopping! Embark on a flavorful journey through Vermont's renowned craft beer scene. I have listed the local breweries below:
Valley Craft Ales - Valley Craft offers a serene setting alongside a meandering river. Their outdoor deck, open during summer months, provides an ideal spot to unwind after outdoor activities. The locally brewed beers complement what many consider the best pizza in town. It's a favorite among locals and visitors alike for its relaxed atmosphere and quality offerings. At night, they typically have performers playing live music- the artists are always posted on their website.
Snow Republic Brewery - Snow Republic stands out for its inclusive, community-oriented approach. The brewery welcomes a diverse crowd, including families and pet owners. During warmer months, the outdoor space comes alive with lawn games and an open-air bar. Sunday afternoons feature live music performances, adding to the convivial atmosphere. It's a place where you can easily spend a few hours, especially on a sunny day.
Beer Naked Brewery- Situated atop Hogback Mountain, Beer Naked Brewery offers panoramic views that are particularly stunning during the fall foliage season. The taproom features large windows and a wraparound deck, both designed to showcase the surrounding landscape. Their beer selection is solid, and they offer pizzas that pair well with their brews. Many hikers, ourselves included, have made it a habit to stop here after trekking the nearby Mt. Olga Trail, finding it a fitting reward for the climb.
Visit Brattleboro's Farmer's Market (Saturday 9am-2pm). Take a short drive to nearby Brattleboro for one of the state's best farmer's markets. Open every Saturday from May to October, this vibrant market showcases local produce, artisanal cheeses, freshly baked goods, and handcrafted items. It's a great way to experience the flavors and craftsmanship of southern Vermont.
Visit the Wilmington Antique and Flea Market (Saturday and Sunday). Treasure hunters won't want to miss this weekend market. Open seasonally, it features a rotating selection of vendors offering everything from genuine antiques and collectibles to handmade crafts and local products. It's an excellent spot to find unique souvenirs or one-of-a-kind pieces for your home.
Where to Eat Lunch:
Village Roost - This is the perfect place to pick up a quick sandwich before a long hike or a day on the boat. All of their ingredients are locally sourced, organic and non-GMO! My breakfast order is always the "Burrito" (add bacon) and a matcha latte. For lunch, I usually try to switch it up because there are so many options but I always find my way back to the "Happy Hen" (add bacon of course). There is also a little shop and dining area in the back if you're in no rush and want to eat in-house.
Snow Republic Brewery- This is the perfect place to hang out with friends to eat, drink and enjoy. The chicken sandwiches are to die for! If you're into spicy, order the "Inferno"- it will not disappoint. During the summer's blueberry season they run a special chicken sandwich called "Pump Up The Jam"- think truffle, blueberry jam, and goat cheese atop a perfectly crisped chicken sandwich (my mouth is watering writing this). Another great option, and a bit healthier, is the "Arthur Ave." If you are not into sandwiches, The diverse menu also features wings, fries, salads, and pizza, ensuring something for everyone.
1846 Tavern- On the weekends they typically run a "buck-a-shuck" oyster special, making it a must-stop spot after a day on the boat. Beyond the oysters, the tavern menu offers salads, sandwiches, and artisanal cheese boards perfect for light nibbling.
Where to Eat Dinner:
Folly- I'm almost reluctant to share this hidden gem, my personal culinary sanctuary. Nestled in a charming house whose main floor was converted into an intimate restaurant, Folly has stolen my heart. The husband, a visionary chef, creates ever-changing menus that never fail to amaze me, while his wife gracefully manages the intimate dining room. Each visit feels like being at a friend's exclusive dinner party. I've lost count of the memorable meals I've enjoyed here, marveling at how they transform fresh, local ingredients into edible art. With only four guests per reservation, dining at Folly is special. I always make an evening of it - savoring wine, trying every course, and cherishing each moment. It's more than a meal; it's an experience I can't help but treasure.
Alpenglow Bistro- This restaurant offers a cozy Alpine retreat experience. The menu blends influences from Switzerland, Germany, Austria, and France, using locally sourced ingredients to create memorable dishes. For the best experience, grab a seat in the intimate tavern. Nick and I often enjoy the bar, where our friend Jeff's friendly service adds to the warm atmosphere. While the seasonal menu always impresses, my go-to is the "Roasted Hünchen". The chicken is consistently excellent, complemented by creative, seasonal sides that showcase Vermont's finest produce.
Sawmill Bar & Table - Just a 15-minute drive from Wilmington, nestled in the charming town of West Dover, lies a culinary gem: Sawmill Bar and Table. This establishment offers a sophisticated twist on rustic American cuisine, deeply rooted in the verdant heart of the Green Mountains. At Sawmill, local flavors take center stage. The kitchen team works closely with small Vermont farms, carefully selecting ingredients that capture the unique essence of the Northeast. Their goal? To transform these local treasures into elevated versions of classic American favorites. While every item on the menu is a testament to Sawmill's commitment to quality, two dishes stand out as personal favorites the "House Made Pappardelle" and the "Grilled Hanger Steak."
Where to Get the Best Cocktails:
Alpenglow Bistro- Cozy alpine vibes, sophisticated cocktails
Bar and Bottle- simpler setting, fresh cocktail ingredients, master mixologist
Red Door- speakeasy feel, eccentric and sophisticated cocktails
The Hermitage Inn- luxury bar, well-balanced and finely crafted cocktails
Summer Events You Don't Want to Miss:
There is always something to celebrate in Southern Vermont! While dates may shift annually, these events typically occur on consistent weekends. For a comprehensive list of Southern Vermont events, click HERE. I have included a list of my favorites below:
Blueberry Fest (Late July - Early August)
Transform downtown Wilmington into a blueberry lover's paradise! Local eateries line the streets with tents, offering blueberry-inspired dishes and cocktails. Stroll, sip, and savor the flavors of summer in this charming setting.
Brew Fest at Mount Snow (Labor Day Weekend)
Bid farewell to summer and welcome fall with Vermont's finest brews. [Purchase tickets here]. Gather your friends, bring blankets or chairs, and enjoy a relaxed afternoon of exceptional craft beers and delicious local food truck fare against the backdrop of Mount Snow.
Adams Family Farm Concert Series (August - Mid-October)
Experience the magic of live music in a picturesque farm setting. Cozy up to a crackling bonfire, sip on craft beverages from the mobile bar, and indulge in the food truck offerings. With admission ranging from $15-$30, this series offers an unforgettable blend of music, nature, and community [Details Here].
Riverside Music Series at Ratu's (Mid-July - Mid-October)
Live music, RVQ Smokehouse food truck, and Club Car cocktails [Details here].
This charming Vermont town, with its blend of natural beauty, outdoor activities, and small-town warmth, offers a perfect summer escape. Whether you've hiked the Green Mountains, explored local shops, or savored farm-to-table delights, Wilmington leaves an indelible mark on your heart. So pack your hiking boots, bring your appetite, and prepare to fall in love with this enchanting corner of Vermont. The mountains are calling, and your peaceful weekend escape to Wilmington, Vermont is waiting!
Here's to the road less traveled and the stories yet to be told... Keep Wandering!
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