STORY BY BENJAMIN LERNER
PHOTOGRAPHY JIMMY iENNER, Jr.
To reach Wilmington, follow Route 9 through Southern Vermont’s idyllic Deerfield Valley. Wilmington is home to numerous stylish boutiques, welcoming inns, and fantastic restaurants. Its surrounding mountains and forests provide phenomenal outdoor activities in all four seasons, including skiing, snowboarding, hiking, biking, swimming, and kayaking. Pack your bags, and make sure to bring your adventurous spirit—it’s time to enjoy a remarkable weekend in Wilmington!
FRIDAY
3PM
As you approach Wilmington, Route 9 will turn into Main Street. While proceeding through town, you will come upon the Wilmington Village Historic District. Spanning the majority of downtown Wilmington, this pleasant neighborhood has earned the honor of being listed in the National Register of Historic Places. Upon arriving in the heart of downtown Wilmington, park your car on West Main Street and check in to The Wilmington Inn. Located a stone’s throw from the banks of the Deerfield River, this inviting inn offers cozy accommodations, spacious suites, and an on-site restaurant and bar that serves up delicious cuisine and Vermont craft beverages. Whether you’re spending the night in their Main House or Carriage House, you will find splendid hospitality and amenities, which bridge the gap between country comfort and modern convenience. For travelers in search of an ideal destination for a celebration, corporate event, wedding, or family reunion, The Wilmington Inn hosts events of up to 50 people indoors and 125 people outdoors. The Main House and Carriage House can also be rented out exclusively for private gatherings. For a boutique hotel experience that never disappoints, book a room at The Vermont House. With top-shelf service, roomy and well-decorated common areas and suites, convenient parking, visually-arresting architecture, and an on-site wine bar, this 19th-century Colonial Inn perfectly represents the hospitable spirit of Wilmington. Drop your bags, take some time to acclimate, and let your cares melt away – your marvelous vacation in Wilmington is just beginning!
4PM
On a Friday afternoon, a plethora of fulfilling sightseeing activities can be found on the streets of the Wilmington Historic Village District. For those who wish to fully immerse themselves in the compelling history of this storied Vermont town, a pamphlet with a self-guided historic walking tour is available (free of charge) at the Southern Vermont Deerfield Valley Chamber of Commerce office on West Main Street. The tour includes dozens of stunning structures, such as The Crafts Inn and Memorial Hall, which stand side-by-side on West Main Street. Throughout the year, the Wilmington Historical Society also offers in-person guided tours, which are overseen by their knowledgeable staff members. The tour features detailed descriptions of the structures that played a pivotal role at the apex of Wilmington’s industrial era in the 19th Century, as well as Wilmington’s cultural evolution during the tourism surge in the early 20th Century.
The Crafts Inn and Memorial Hall were both built in 1902, and were designed by the esteemed New York City architectural firm of McKim, Mead, and White. Lauded by prominent architectural scholars as notable innovators in the field of modern American architecture, their portfolio includes The Boston Public Library, The Brooklyn Museum, the Rhode Island State House, The National Museum of American History, and the famed “Naumkeag” estate in Lenox, Massachusetts, among many others. The same breathtaking characteristics that are visible in their most noteworthy New England Shingle-Style estates are also beautifully exemplified through The Crafts Inn and Memorial Hall. The massive and imposing wood frame, cedar shingles, and central gambrel roof of the Crafts Inn creates an atmosphere of rustic resplendence, hearkening back to the bustling days of Wilmington’s tourism boom. In its heyday, the Inn hosted high-profile dignitaries such as U.S. President William Howard Taft and the revered American Naval Admiral, Matthew Calbraith Perry. Today, it stands as a well-renowned lodging destination, which welcomes many loyal guests who come to Wilmington in all seasons. Down on South Main Street, the Pettee Memorial Library stands as a superb example of Classical Revival brick architecture. A sculpture of a Union soldier is located in front of the entrance, which boasts heavy oak-paneled doors and ionic columns. The equally-iconic Molly Stark Statue can be found in the shadow of the Crafts Inn on West Main Street. The statue pays tribute to Elizabeth Page “Molly” Stark, the wife of the celebrated Revolutionary War General, John Stark. Molly Stark remains a beloved symbol of American patriotism to this day. Her courage and self-reliance epitomized the honest, persistent, and hard-working values of the Green Mountain State.
Those who wish to take in a more contemporary artistic spectacle should stroll down to Beaver Street to feast their eyes on the Beaver Street Art Project. A series of gorgeous, steel-mounted two-dimensional sculptures—including depictions of Wilmington’s most treasured buildings and its surrounding natural scenery—are affixed to a wall near the intersection of Beaver Street and School Street. The project came into being as a result of a coordinated effort by the town of Wilmington. It was funded by grants from the Vermont Arts Council, individual donations from Wilmington’s residents, and the Vermont State Government. The piece was fabricated at Payne Junker Studio in Chester and was installed to the delight of Wilmington’s residents and visitors in 2022.
After your Wilmington walking tour reaches its conclusion, head to West Main Street and treat yourself to some retail therapy at Wilmington’s independently- owned shops. Avid readers will adore the literary treasures at Bartleby’s Books and West End Used Books, and the fetching souvenirs at Hayseed Gifts and The Incurable Romantic are hard to beat. Looking to update your closet with some chic, upcycled clothing? Stop in at The Fashion Plate and explore their curated consignment apparel to your heart’s content. For an additional touch of boho-chic finery, continue onward to Pickwell’s Barn and peruse their assortment of versatile sartorial staples. A trip to The Vermont Bowl Company is a must for travelers who are interested in sprucing up their kitchens with high- quality, Vermont-made wooden bowls or cutting boards. Connoisseurs of cordials and cannabis will feel right at home while browsing the selection of liquors, wines, and cannabis products at Ratu’s Liquor & Market.
7PM
After freshening up in your well- appointed guestroom, why not book a dinner reservation at one of Wilmington’s best restaurants? 19 South Main serves up filling Italian and pan-European dishes
made with local ingredients, and their house-made pizzas are satisfying and scrumptious. On West Main Street, Alpenglow Bistro offers a tempting assortment of Alpine and Swiss culinary classics, such as Bavarian pretzel boards, savory crepes, and French patisserie tarts. Pour a celebratory glass of cognac, port, or single malt scotch and toast to the good life. Your sensational sojourn in Wilmington has only just begun!
SATURDAY 8AM
Rise and greet the day with an energizing breakfast at Dot’s Restaurant on West Main Street. Put in an order for an omelet, waffles or pancakes with extra Vermont maple syrup, or grab some muffins,
bagels, or cinnamon rolls to go. Make sure to bring extras for any friends or loved ones who might be traveling with you— it’s always good to bring some tasty baked goods on your outdoor adventures.
10AM
Regardless of the season, Wilmington offers world-class outdoor recreation opportunities. In the colder months, winter sports enthusiasts from all corners of the Atlantic Northeast and beyond flock to Mount Snow Resort on Mount Snow Road in nearby West Dover. With exceptional trails and diverse terrain, Mount Snow offers a high-level, well-rounded winter sports experience. The Main Face is home to many of the best cruiser trails on the mountain, as well as multiple gentle and meandering trails that are ideal for novices who wish to experience a long, continuous ski run from summit to base. The Sunbrook Face features several ungroomed trails, which provide a taste of traditional New England Skiing. The North Face is a challenging proving ground where accomplished ski and snowboard veterans can savor some of the steepest terrain in the Northeast. The terrain parks in the Carinthia area are perfect for skiers and boarders of all experience levels, and are chock-full of tantalizing obstacles, rails, and jumps, as well as Mount Snow’s gargantuan super half-pipe.
Private and group ski and snowboard lessons are taught by Mount Snow’s talented and friendly instructors, and their youth development and competition programs offer emergent winter
athletes the chance to hone their skiing and snowboarding skills. For on-site ski and snowboard rentals, visit Sundance Retail and Rentals or The Grind Tune Shop and Rentals, both of which are located within the bounds of the Mount Snow campus. The Mount Snow Tubing Hill is great for both kids and adults, and guests in search of a pampering respite should book a relaxing treatment or massage at the on-site Naturespa at the Mount Snow Grand Summit Resort. The Grand Summit Resort provides elegant mountainside accommodations, and also houses a health club, an outdoor heated pool and jacuzzi, and a farm-to-table restaurant. For those in search of more affordable lodging, the Snow Lake Lodge is also located on the resort grounds. Harriman’s Farm to Table at the Grand Summit Resort Hotel is an outstanding dining option for both romantic après ski evenings and family dinners at Mount Snow. Toothsome gourmet dishes are made with high-quality locally-sourced ingredients, and the drink menu features Vermont craft beer and specialty drinks made by their expert mixologists. For a refreshing lunchtime bite, pop into Cuzzins Bar & Grill at the Main Base Lodge for a tasty wrap, burger, or salad.
The hills surrounding Wilmington and West Dover are home to some absolutely incredible snowmobiling trails, which offer high-octane wintertime entertainment. The trails are lovingly maintained by a local chapter of the Vermont Association of Snow Travelers (VAST), The Deerfield Valley Stump Jumpers. Working hand-in-hand with local lodging businesses, authorized snowmobile dealers, and VAST, they help visitors and native Vermonters take advantage of the Green Mountain State’s exhilarating snowmobile trails. All snowmobilers who wish to ride on Vermont’s trails are required to have their snowmobiles registered through the Vermont DMV. They are also required to pass a state-mandated snowmobile safety course and pay a nominal fee to VAST. For more information, visit:
vtvast.org or dvsj.org.
When the pristine snowbanks on Mount Snow and its surrounding hills and valleys melt and recede in the springtime and summer, the landscape transforms into a veritable hiking paradise. For a convenient hike close to Wilmington’s historic district, head to the Riverwalk & Hoot, Toot and Whistle Trail. The trailhead for this novice-friendly trail can be found at Reardon’s Crossing, a pedestrian bridge directly off West Main Street that spans the Deerfield River. The trail follows the river for half a mile, offering stellar riverside views. After coming across a second bridge, hikers can choose to walk back across the Deerfield River towards town. Alternatively, they can continue onward on a small loop trail, which serves as the trailhead to the Hoot, Toot, and Whistle Trail. The 1.5-mile trail is built on the old railroad bed of the Wilmington Railroad. It leads to the nearby Harriman Reservoir, which is a magnificent destination for summertime swimming, picnics, and boating. The Mt. Mills West Picnic Area on Woods Road in Green Mountain National Forest and Wards Cove at the end of Boyd Hill Road offer panoramic lakeside views. Both sites are outfitted with multiple tables, which can easily accommodate large visiting families as they bask in the summer sunshine.
More advanced hikers in search of a challenging, yet gratifying outdoor experience will relish the opportunity to test their mettle on the Haystack Mountain Trail. Spectacular vistas await at the highest point of this 5-mile out-and-back trail, which is a well-traveled destination for birding, hiking, and trail running. The trailhead is located on Upper Dam Road, and dogs are permitted on leash. Hikers of exceptional ability who are interested in completing the trek past Haystack Mountain to Mount Snow can take advantage of the Deerfield Ridge Trail. The Deerfield Ridge trail shares a trailhead with the Haystack Mountain Trail at Upper Dam Road. Novice hikers, take heed: this is a difficult, 10.2-mile, out-and-back hike. Hikers should pack extra layers of warm clothing, plenty of food and water, a map, and a communications device. They are also encouraged to safely hike in a manner that is in line with their fitness abilities.
1PM
Whether you’ve gracefully carved a path down the slopes of Mount Snow Resort or hiked to the peak of a majestic mountain, you’ve certainly worked up a considerable appetite by now. Pescatarian gourmands who long for fresh fish will bask in the bounteous selection of seaborne delicacies at Anchor Seafood on South Main Street. Located in a recently-restored building in Wilmington’s Historic Village District, their menu features fresh New England seafood classics such as lobster, mussels, chowder, and rotating daily specials. The authentic Mexican tacos, nachos, and quesadillas at La Casita Taqueria y Mas on South Main Street will tempt your tastebuds with savory splendor, and famished herbivores will revel in the heavenly flavor of their vegetarian taco salad. On West Main Street, Village Roost offers seasonally-shifting signature sandwiches, soups, and salads, many of which incorporate a vast range of international culinary traditions. While you’re there, pick up a coffee, tea, or espresso drink and recharge your batteries. An afternoon of unforgettable shopping awaits you on the streets of Wilmington!
3PM
You likely spent the morning elevating your personal fitness with a spirited excursion to Mount Snow or a Southern Vermont hiking trail, so why not elevate your home décor and furnishings with a
trip to Wilmington’s preeminent secondhand shops, furniture stores, and design studios? Jasper Décor on South Main Street houses an extensive inventory of unique, secondhand gifts, jewelry, and restored furniture. Vintage ceramic pieces, artisan necklaces, and lamps are complemented by an equally diverse assortment of wooden furnishings, all of which are sold for a wonderfully-affordable price. Rock River Restoration on West Main Street specializes in repurposing and restoring old household furnishings in inventive and artistic ways. Their storefront is replete with handmade jewelry, distinctive snowshoe art, and beautifully-restored furniture and accessories, which range from benches and tables to lamps and coasters. Close by on South Main Street, Opa! is home to a broad panoply of fanciful gifts, housewares, kitchen essentials, and gardening products. Pick up some craft ice trays, mason jar lids, local cheeses, and Nordic Ware Cake pans. You’ll thank yourself the next time that you host a dinner party. Quaigh Design Center on West Main Street is an art, craft, and design gallery that has been praised by The Boston Globe and National Geographic Traveler. Their collection features pieces by established, masterful craftspeople, as well as traditional Scottish and Irish Woolens, jewelry, and mohair and wool throws.
For a bright and cheery change of pace, pop into North Star Pizza on West Main Street for some family-friendly afternoon snacks and fun. With a full bar, affordable entrees, and an on-site arcade, pool table, and multiple-lane bowling alley, this laid-back Wilmington hangout is favored by locals and visitors alike. Their mini-golf course is ideal for afternoon excursions in the warmer months, making a trip to North Star Pizza a metaphoric “hole-in-one” in every sense.
7PM
As the sun begins to set over the Deerfield River, the time has come to put on a fashionable outfit and step out for an enjoyable Saturday night on the town. Cultured gastronomes will find extraordinary upscale fare at Folly on West Main Street, where skilled chefs whip up creative dishes with unparalleled flair. After savoring the last bite of your chosen dish, get ready to embark on a tour of Wilmington’s beloved pubs and alehouses, starting with The Maple Leaf Tavern on North Main Street. Discerning bon-vivants will marvel at their astonishing array of signature cocktails and draft beers, which are nicely contrasted by the complex and nuanced beer offerings of Valley Craft Ales on North Main Street. The owners of Valley Craft Ales have recently converted the site of a shuttered Wilmington hospitality landmark, The Old Red Mill Inn, into an innovative new brewery and Inn. Valley Craft Ales are currently sold in dozens of stores throughout the state, and the management of the brewery have opened up an on-site taproom, as well. Valley Craft Ales is currently accepting reservations for overnight guests, and they plan to expand their brewery operation and beer offerings as the project continues to develop.
After stopping in at Valley Craft Ales, head to Wilmington Village Pub on South Main Street to spend the rest of your evening in a lively and joyful setting. Open late on Fridays and Saturdays, this jolly and welcoming bar has a wide-ranging beer list and eclectic cocktail menu. Tip back a favorite beverage, gather together with some old or new friends, and let the good times flow like the rushing waters of the nearby Deerfield River.
If you long to luxuriate in a picturesque nature escape that lies beyond the reach of Wilmington’s downtown district, book a room at the White House Inn on Route 9. The White House Inn has exquisite décor and architecture, tasteful accommodations, and a terrific on-site Italian restaurant (Clara’s Cucina Italiana). It is an ideal setting for a sublime getaway in a verdant Southern Vermont valley. In the mood for a casual meal? Skip the fanfare and head to the nearby Wilmington House of Pizza on Route 9. Take a slice to your room, kick off your shoes, and lose yourself in a priceless moment of indulgent relaxation.
SUNDAY 8AM
Sunday mornings call for hearty, unpretentious breakfast fare served with a sincere smile. After some pancakes and eggs at Cup N Saucer restaurant on Route 100, pop over to 1a Coffee Roasters on West Main Street for some locally-roasted, single origin coffees. The owners of 1a Coffee Roasters, Brian and Chrystal Holt, are deeply passionate about their craft.
They are also open to speaking with visitors who come to their coffee bar about the best methods for making exceptional, homebrewed java.
10AM
Now that you’ve filled up on breakfast treats and a flavorful morning beverage, it’s time to make the most of your last day in Wilmington. Travelers looking to take things at a slower pace, de-stress, and spoil themselves with a rejuvenating wellness treatment should book a session at Serenity Spa on West Main Street. Located on the grounds of The Crafts Inn, the Serenity Spa provides a full-range of therapeutic massage, foot and hand, and energy work treatments. Signature services include CBD deep tissue massages, hot stone massages, and “No Touch” Marconic Energy treatments. Guests are also granted access to the on-site pool and hot tub for a small additional fee.
For more outdoor exploration opportunities during the warmer months, make a beeline for the Mount Olga and Tower Trail Loop in Molly Stark State Park. Located off of Route 9, this hike is relatively accessible for hiking newcomers, and offers fantastic views of the surrounding mountains. The hike culminates on a hilltop near a fire lookout tower. The tower has recently been closed due to recent construction efforts, so visitors are encouraged to check on the Molly Stark State Park website for updates before visiting. Travelers who come to Molly Stark State Park are required to pay a fee upon entrance. Parking is available on-site, as well as access to campsites and a picnic area.
Cyclists and hikers interested in an invigorating and comprehensive tour of Windham County’s natural scenery highlights should follow the Valley Trail north from West Main Street. The 12.3- mile trail is dotted with multiple trailheads and access points, allowing hikers and bikers to cover as much of the trail as they see fit. In the colder months, the trail is also ideal for snowshoeing and Nordic skiing.
In addition to Harriman Reservoir, Lake Raponda also offers family-friendly swimming and lakeside merriment during the summertime. Access to Green Mountain Beach at Lake Raponda can be found on Lake Raponda Road. An easy, quick 0.3-mile hike around the Town Forest Loop branches off from a trailhead at the Green Mountain Beach Parking lot. Numbered signs identify different specimens of local trees, including beech, paper birch, sugar maple, red spruce, and hemlock.
North of Wilmington Center, Boyd Family Farm on East Dover Road welcomes all visitors and families. Guests who come to Boyd Family Farm during the summer can pick their own berries and flowers. Autumnal visitors will find seasonal vegetables, such as pumpkins, and guests who come during the Holiday season will discover all manners of decorative greenery for sale, including wreaths, centerpieces, and Vermont-grown Christmas trees.
1PM
As your Wilmington vacation draws to a close, stop in at River Valley Market and River Bend Farm Market for some fresh produce and Vermont food products, or pick up a delectable sandwich or pre-made meal from their deli counter. Jezebel’s Eatery on West Main Street is also well-stocked with appetizing Take-n-Bake home-cooked items, which make great road snacks. Their on-site tavern is a wonderful place for a sit-down meal or final festive beverage. Before you hit the road, pay a visit to the 1836 Country Store on West Main Street. Pick up some Vermont souvenirs, maple syrup, and some homemade Vermont fudge, and give the gift of Green Mountain State goodness to your friends and family.