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New England by Heart

Wilmington VT

River Bank Park Stone Bench - Wilmington VT

Wilmington, Vermont is a town that seems perpetually on the brink of either decline or rebirth, and it’s not entirely clear which way it will eventually go. The devastation of Tropical Storm Irene in 2011 was a major setback for a town whose main industry is tourism. That said, the amount of restoration and build-back has been incredible and major kudos go to those whose efforts have made this happen.

The setting couldn’t be lovelier, sitting at the southeastern edge of the Green Mountain National Forest, at the crossroads of two iconic scenic roads – Route 9 (known as the Molly Stark trail) spanning the state east-west, and picturesque Route 100 spanning north-south. As a side note, I was amused to find the north-south and east-west roads intersecting in town all named Main Street: East Main Street, West Main Street, North Main Street and South Main Street. Good old New England practicality at its best.

The two Deerfield River branches converge here from north of town, flowing into lovely Lake Whitingham (Harriman Reservoir), which provides swimming, boating and fishing opportunities. Along with fall’s foliage and winter’s ski seasons, that makes this a year-round destination.

Wilmington’s cozy downtown radiates out from its central intersection, and there are currently enough compelling shops and eateries in town to warrant a couple hours of pleasant browsing and lingering over a meal or cup of coffee. An excellent brewery rounds out the appealing offerings. There are also several inns, two notables right in the center (Crafts Inn and Vermont House) and others scattered beyond.

The downtown buildings are mostly 19th and early 20th century buildings, remarkably undisturbed by the modern tear-down-and-replace attitude that has impaired the aesthetics of many downtown areas. There are more than 60 historic buildings spanning multiple architectural periods, each with its story to tell.

But strolling around makes clear that there are still worn and even empty buildings interspersed among the active businesses. Many were decimated by the 2011 flooding, which raised the river 25 feet and caused $13 million in damage. With climate change, the threat of future flooding and snowless winters are worrisome.

Nevertheless, the town has endured setbacks before, including the flood of 1938 and the closure of nearby Hogback Mountain Ski Area in 1986. The town has much going for it and may just be waiting for some industry to kick it back into high gear. It calls out for more entrepreneurs to make this pretty little village a mecca for boutique shops carrying local artisan wares, clothing, ski gear and gourmet goods.

With the Molly Stark Trail and Route 100 running through it, the draw of Harriman Reservoir, and easy excursion distance to all that southern Vermont and north-western Massachusetts have to offer, Wilmington can be a star attraction, effectively competing with the likes of Stowe and Woodstock.

Named for Spencer Compton, the first Earl of Wilmington in England, Wilmington has an interesting, if confusing beginning. It was first chartered in 1751 by Benning Wentworth, the governor of the colony of New Hampshire. There were a good number of grantees in that charter, who surveyed the town and divided it up among themselves. However, only two of them are known to have actually shown up to settle here.

A second charter was granted in 1764 to different grantees, and though no settlement came of it, disputes naturally ensued. The first charter eventually prevailed, and more settlers slowly arrived, with fourteen families established by 1771. Lest you think that this was an easy trek, keep in mind that there were no roads to speak of. These intrepid souls had to find their way to this very wild and remote place mostly along footpaths.

Nevertheless, they managed to form a community centered on Lisle Hill, eking out their living with mills and farms. Like so many early settlers in the remote wilds of New England, they were necessarily a hardy bunch. A legendary story is of one Mrs. Titus who, tired of hearing a lodger in her house bragging that no man could throw him, left her weaving loom long enough to throw him to the ground, declaring that there was one woman who could do it.

The community established its tiny local government, and through the remaining years of the 18th century, voted on various important matters, including electing a representative to the General Assembly, establishing a treasury, raising funds for highways, procuring a minister to tend to their souls, and sending off soldiers to fight with General Stark in Bennington in 1777, and to fight in the War of 1812.

With the building of the “Great Road” from Brattleboro to Bennington in 1828, it became clear that the village center belonged closer to the road and the river, and so it was done around 1833. This was quite the endeavor, with eight buildings moved by ox-drawn carts. Four of those still remain, including Norton House (the oldest), which sits beside the 1836 Lyman House, which currently houses an eatery and the 1836 Country Store.

Life went on, with a diversity of farming and mills. But in 1885, a harbinger of change occurred. The Hoosac Tunnel & Wilmington Railroad – otherwise known colloquially as the Hoot, Toot & Whistle railroad – was built to connect Readsboro, Vermont to Rowe, Massachusetts. The eleven mile narrow gauge railroad moved lumber from the various mills along the river.

Naturally, the good people of Wilmington wondered why it shouldn’t extend another 14 miles to reach Wilmington, and so it was done, with the new stretch mostly servicing passengers who wished to enjoy the fresh air of Wilmington. The ensuing economic boon carried Wilmington into a new era. Visitors invested in seasonal properties and others decided to stay permanently. Winter activities blossomed, with sledding down mile long routes, a hint of the well-known Vermont ski industry to come.

In 1924, the construction of the Harriman Dam flooded the valley of Mountain Mills, drowning the village and a good many fertile farms. But Wilmington was already leaning more towards tourism, and the newly formed lake added to its appeal.

This is pretty much where Wilmington is today – supported by its tenuous hold on tourism. Its economic plan focuses on a well maintained and attractive downtown, including expansion outside the flood hazard area and making the town more flood resilient, creating incentive and promotional plans for new and existing businesses, and attracting new and younger permanent residents.

Time will tell if these efforts pay off with a strengthening of tourism. The establishment of a major business that could employ a good number of well-paid employees wouldn’t hurt, either.

The Deerfield River headwaters are north of Wilmington, with the north and west branches converging at the northern end of Harriman Reservoir, then onward through the dam to eventually empty into the Connecticut River, descending almost 1,100 feet along the way. This made the river great for mills in the 19th century, and hydropower beginning in the early 20th century. There are a total of ten licensed dams along the river.

But lest you think that this has resulted in a sad situation for the river, be assured that it has not. Despite there being 36 towns within its basin (the areas draining into the river), the total population of those towns is less than 50,000, and 80% of the basin is forested. Nine major tributaries empty into this clean, scenic river, and it’s a favorite for fishing, white water rafting and other water recreation, particularly on the reservoirs created by the dam, Harriman being the largest. (Check out this wonderful article on the Deerfield River in Estuary Magazine).

Self-Guided Tours

About my self-guided tours

My Walk and Drive With Me tours are self-guided and designed to take no more than 2-3 hours. This allows you to easily incorporate them into an overall travel itinerary or simply enjoy one as a morning or afternoon excursion.

Other Excursions & Experiences

In Town

Harriman Reservoir (Lake Whitingham)

Harriman Reservoir (Lake Whitingham)

Harriman Reservoir, also known as Lake Whitingham, was created in 1923 via the damming of Deerfield River by the New England Power Company, part of a hydroelectric power project. This beautiful lake covers over 2000 acres and is 180 feet at its deepest. With over 28 miles of undeveloped shoreline, it also contributes to a true sense of being away from it all.

For picnicking, swimming, and boating, or simply enjoying its beauty, it can’t be matched. Here are areas to check out – all are quite pleasant with picnic tables and access to the water for swimming and paddling. The first two have boat launches.

  • Fairview Avenue picnic area: Along with the Fairmont Launch, this is on the upper east side of the lake at the end of (naturally) Fairview Ave. This is a great spot to admire the lake, with or without a picnic, with a dock that stretches out into the lake. This is also a terminus of the 3.8 mile (round trip) Hoot, Toot and Whistle Trail, a flat, easy trek through the woods and along the river, which ends at the Reardon Crossing Bridge downtown.
  • Mt. Mills West Picnic Area: Across the lake from the Fairview Avenue picnic area, this is another nice picnic area and good place to launch your kayak.
  • Ward’s Beach & Boat Launch – almost halfway down the long lake at the end of Boyd Hill Rd, is another great picnic area, where you can also scramble a bit along the rocky shore.
Hiking in Wilmington


There’s some good hiking in and around Wilmington, and the Wilmington town site provides information on area trails. Following are the choice recommendations in Wilmington.

  • Haystack Mountain Trail: This is a 4.1 (total in and out) moderately challenging trail that has beautiful views at the summit. You can be done in a couple hours.
  • Mount Olga Trail: This is a moderately challenging 1.8 mile loop trail in Molly Stark State Park. The key draw is thenMount Olga fire tower – otherwise, there are no particular views. There’s a picnic area at the base. At the time of this writing the fire tower is closed for repairs, so be sure to check the website.
  • Hoot Toot and Whistle Trail: Beginning at the Fairmont Launch swimming and picnic area and ending at the There’s also an easy hiking trail here along the Deerfield River, whimsically called the Hoot Toot and Whistle Trail. A good way to work off some of that picnic.

The Art of Humor Gallery

Dedicated to the art and life of humorous illustrator and cartoonist Skip Morrow, the Art of Humor Gallery is a great way to lighten the mood. Famous for his offbeat humor, Skip lived in Wilmington from 1974 until his death in 2019, and personally greeted visitors to his gallery. His wife Larraine now stands in his stead and delights in showing off his work. The gallery truly does justice to the late humorist. A free book is included in the price of admission, and admission is also good toward any purchases you make.

Note that as of this writing, the property is up for sale, so check first before heading up to this wonderful gallery. Be quick, so you don’t miss it. The website will continue on for fans of Mr. Morrow.


Glory Hole & the Dam

Glory Hole & the Dam

The dam that created the Harriman Reservoir includes an unusual feature called a “morning glory”, a massive doughnut shaped structure, where water pours into and travels way down onto the other side of the dam to continue its journey along the Deerfield River. Purportedly, when the water levels are low, you can see the old foundations of Mountain Mills, the logging village that existed here before the dam was built.

You have to work a little to find this, but Google maps seemed to know the way. There’s a small sign on Route 100 west of Whitingham that announces Dam Rd, which is easy to miss. This skirts the west side of the lake and you eventually will come up beside the perfect spot to see the Glory Hole from above, where it is most impressive.

Drive on further to arrive at the picnic area. There is a fence and a no trespassing sign between the picnic area and the dam, but when we were there, the gate was open and we were able to walk up onto the dam, which affords a fabulous view of the lake and of the river far below, and a closer view of the Glory Hole. This is by no means treacherous – the top of the dam has a wide gravel trail and the grassy slope to the river, while steep, is not frighteningly so. You can take this from me, as I have a fear of falling and was not nervous at all.

Hogback Mountain View, Shop & Brew

Hogback Mountain View, Shop and Brew

Along the Molly Stark Trail in Marlboro is a pull-off area with a stupendous view, a country store, a brewery and a distillery. Once you park (and it can be tricky in peak season), you’ll want to spend some time admiring the long views. After you’ve ogled for a bit, shop at the Hogback Mountain Country Store for fudge and all manner of souvenirs. Go outside and ogle some more, and then maybe meander over to Metcalfe’s Distillery to taste their Maple Bourbon. Ogle some more, then finish this spot off with pizza and brew at Beer Naked Brewery.

In Marlboro, the Molly Stark Trail (Route 9) traverses its highest point, between Hogback Mountain to the north and Mount Olga to the south. Offering stunning views, it’s arguably the highlight of the trail.

With the opening and 1936 dedication of the new, paved highway connecting Brattleboro to Bennington, businesses were quick to arrive at this lovely spot, beginning with the Marlboro Tavern (with rooms for weary travelers), the Hogback Mountain Country Store, the Skyline Restaurant, and the Marlboro Inn.

Skiing naturally followed, with slopes, trails, and a tow on Mount Olga (not on Hogback Mountain, despite the name). Over the years, the ski area expanded and thrived. That is, until the 1970s, when it began to struggle against competition from nearby Mount Snow and Stratton Mountain, along with dwindling snowfall starting in the late 70s. By 1986, it closed, never again to open, despite a few subsequent failed efforts to resurrect it. Remnants of the operation still can be seen today, slowly being absorbed back into Mother Earth. Thanks to efforts of local citizens to prevent development, much of the land is now in the hands of the Vermont Land Trust, Vermont Housing and Conservation Board, and the Town of Marlboro.

Of all the original businesses, only Hogback Mountain Country Store remains. Along with the amazing views from their huge deck, they offer up souvenirs, cheeses, creemees, apple cider donuts, homemade fudge, maple syrup and more. This is most definitely catered to tourists, but you will find some nice things here.

Mount Snow

Mount Snow

One of the first ski resorts on the east coast, Mount Snow opened in 1954. Today, it boasts 601 acres of skiing with a 1,700 foot vertical drop, 19 ski lifts and 83% snowmaking coverage, it’s no slouch of a ski resort. For summer and fall fun, there’s a scenic chair lift, a bike park, a golf course and miles of hiking trails. The resort boasts several eateries, a few of which are open in summer and fall.

Natural Bridge State Park

Natural Bridge State Park

Natural Bridge State Park is an abandoned marble quarry features a naturally formed arch of marble that spans the Hudson Brook, which tumbles through a 60 foot gorge. The arch is the only natural white marble arch in America. Also here is a man made marble dam, and of course, the old quarry itself. A small visitor center orients you to the history of the place, and there are picnic areas, a sculpture garden and a nature trail to round out your visit.

As of this writing, years of neglect and flooding have caused damage to walkways and platforms, and access to the bridge and other parts of the park are closed. The Department of Conservation and Recreation is leading a multi-year project to redesign the park. 

Massachusetts Museum of Contemporary Art (Mass MoCA)

Massachusetts Museum of Contemporary Art (MASS MoCA)

Opened in 1999, MASS MoCA is an art museum and performing arts center that has consistently gotten rave reviews from visitors and critics alike. Occupying a very large and old mill building gives it a very industrial feel and a scale that allows for breathtaking displays of innovative art. This is a museum you do not want to miss.

Notable Shopping Experiences

I invite you to search online for overall shopping venue options and ratings. My focus here is to point out those places that have historic or iconic value.

Vermont Bowl Company

Vermont Bowl Company

Hop in the car and drive west on Route 9 to the Vermont Bowl Company just a half mile west of the village center. This is its factory headquarters and there are more than bowls at this artisan woodshop – cutting boards, chargers (those things you put under plates), puzzles, signs, lazy susans, ornaments, even wooden drinking cups! And if you get tired of all the wood (how could you), they also carry some local food products and pottery.

While you’re there, stop in at Starfire bakery to pick up some truly delectable baked goods, because why would you pass up a bakery?

Events not to Miss

Every town has some number of events throughout the year. Some have staying power, some don’t. Some are geared to special interests, like road races, while others appeal to a wide audience. Even some special interest events can become so iconic that they attract wide swaths of audiences and participants. My goal it to bring forth those events in a town (or nearby) that are enduring and treasured by the local community. For other events, be sure to check the local listings.

Wilmington Antique & Flea Market

Wilmington Antique & Flea Market

Every Saturday and Sunday, from mid-May to mid-October, vendors set up their wares at the 10 acre Wilmington Antique & Flea Market, about a mile east of downtown on Route 9. Running strong since 1983, you can find the new and old, antiques and crafts, homemade foods and more. A classic flea market for a fun couple hours on the weekend.

Notable Eateries & Watering Holes

I invite you to search for overall options and ratings on eateries and watering holes. My focus here is to point out those places that have historic or iconic value.

Dot's Restaurant

Dot’s Restaurant

Dot’s Restaurant is such an iconic spot in Wilmington, that even though it was fairly well demolished in the 2011 flood, the town refused to let it go, rallying behind owners John and Patty Reagan to rebuild. A sane economic response would have been to let it go, but this was not about economics. It was about saving a treasured eatery that was as much about community exchange as it was about noshing.

And not just for locals – purportedly, every Vermont governor, along with other politicians, appears here for a photo opp and to promote their campaigns.

The building dates to 1832, originally a post office, then a general store, and became a diner in 1930. The building was destroyed by the 1938 flood and rebuilt. John Reagan bought Dot’s in 1981, married Patty in 1988, and they ran it together until John’s death in 2017. Patti persevered and Dot’s continues it’s tradition. 

Creemee Stand

Creemee Stand

Creemee Stand is lauded as serving one of Vermont’s best maple creemees (Vermont’s name for soft serve ice cream), made with maple syrup from nearby (within eyesight) maple trees. They also carry hard scoop ice cream from Wilcox, Vermont’s oldest ice cream manufacturer, for those in your party who are just not maple or creemee fans (scold them).

Maple creemees are a serious thing in Vermont, and I’m always on the lookout. Sadly, we were in Wilmington too late in the season to experience this bit of Vermont joy, but I will be back.

Creemee Stand, with its true New England practical name, has been operating seasonally since 2002 and has become a local institution. If you’re here in the summer season you would be quite remiss if you passed up this treat. Be aware that it is cash only.

Valley Craft Ales

Old Red Mill - Valley Craft Ales

The Old Red Mill on North Main Street was originally built in 1828 by Richard Waste as a grist mill, later transitioning to a lumber mill. In the 1890s, it was used by the Readsboro Chair Company to manufacture chair stock. Over the years, wooden water wheels were replaced by metal wheels, and eventually turbines. A fire partially destroyed the building in 1900 and it was rebuilt in 1902-03, with some original features remaining. Since the 1930’s, the building has been used as an inn and various restaurants, currently run by the excellent Valley Craft Ales.

Maple Leaf Tavern

Dr. Pulsifer’s House / Maple Leaf Tavern

The Maple Leaf Tavern on North Main Street occupies one of the original eight buildings moved from Lisle Hill in 1833, where it had housed the medical practice of Dr. Billings Pulsifer. In its new location on North Main Street, the ground floor was, at some point, extended out from the main building, and a porch constructed above that. The shed dormer likewise was probably added at a much later date.

There is an interesting story about the Maple Leaf Tavern that ties it in a strange way back to Dr. Pulsiver. The first Maple Leaf Tavern went into foreclosure in 2018 and was snapped up at auction by two brothers who grew up in the area. One of those brothers went off to pursue a medical career, but now finds himself running this particular tavern in Vermont. Perhaps the ghost of Dr. Pulsifer called back a kindred spirit.


Two Tannery Road

Two Tannery Road

Two Tannery Road was owned in the early 1900s by President Theodore Roosevelt’s son and daughter-in-law, and the President was known to visit as a retreat. The building has been moved twice, once in the late 1700s from Marlboro and again to its current location in the 1940s after the Roosevelts sold it.

The tavern sports an antique bar from the original Waldorf-Astoria in New York City, removed in 1919 at the onset of Prohibition, adding another twist of interesting history.

Add to that some upscale dining, and this is a winner.

Notable Lodgings

I invite you to search online for overall options and ratings on lodgings. My focus here is to point out those places that have historic or iconic value.

The White House Inn

The White House Inn

You can’t miss The White House Inn, a picture-perfect Colonial Revival mansion perched up on a hill to the east of Wilmington on Route 9. Built as a summer home for lumber baron Martin A. Brown in 1915, the inn has been beautifully restored. The interior spaces include many of the original details, including 14 fireplaces, portions of the “Italian Landscape” wallpaper (the rest being reproduction), and an antique call system, and of course much of the woodwork detailing. A secret staircase hidden behind a china cabinet “door” leads up to a sitting room used by Martin’s wife, Clara.

Brown grew up in Whitingham, he went from clerking to leading several companies in the area. He acquired 600 acres east of town, called Beaver Meadow Farm, and commissioned the building of the home for himself and Clara.

With all this history and beautiful architecture, balanced well with modern amenities, the White House Inn is one of the best accommodations in the area.

The Vermont House

The Vermont House

In the heart of Wilmington’s downtown, The Vermont House adds charm as well as accommodations for those wanting to be in the thick of activity. A three-story, eleven room Greek Revival inn, it opened in the mid-1800s as an inn and tavern serving stagecoaches traversing the Green Mountains between Brattleboro and Bennington. Its history is in keeping with its longevity, having hosted the first Old Home Week dinner in 1890, and offering up its porch as the reviewing stand for parades. Its third floor was used as a dance hall, with the third floor porch no doubt providing a welcome place to cool down between sets.

The Crafts Inn

The Crafts Inn

Along with Memorial Hall next door, The Crafts Inn was designed by architects of the notable New York architectural firm of McKim, Mead & White. The site formerly hosted Wilmington’s first hotel, which was destroyed by fire in 1885, along with a number of other buildings.

Crafts Inn (then known as Childs Tavern in honor of Major Childs) is a New England shingle-style hotel commissioned in 1898 and opened in 1902. It features a wide front porch with paired Doric columns that fairly cries out for a rocking chair and a glass of iced tea. The inn was meant for extended stays and saw several expansions in the early 20th century. Famous guests reportedly include Presidents Taft and Coolidge, Norman Rockwell, and Admiral Perry.

In the 1980s, it transitioned to timeshares, and many units are available for booking stays. The exterior of the inn is very charming, with lovely gardens and the Deerfield River in back. Inside, it could use a little updating, but you can’t beat its location in the heart of town.


Colonel Williams Inn

Colonel Williams Inn

The Colonel Williams Inn is a historic Georgian Colonial home commissioned in the early 1770s by, of course, Colonel William Williams. The inn retains many of its early features, and is decorated simply in keeping with its modest colonial farmhouse architecture. The barn, once housing farm animals, is now a charming wedding venue. The inn sits up on a hill with views of the surrounding mountains.

It’s always a pleasure when inn owners ferret out and share the history of old homes, and the current owners (the Marinaro family) have done an exceptional job with a detailed history, which I summarize here.

Colonel William Williams, a member of the famed Williams family of Williamstown, MA, brought his family to Marlboro in 1769, building the home that would become the inn. The good Colonel was a model citizen, promoting Marlboro as a great place to live, and then so with Wilmington, to where he adjourned in 1777. He fought in the French and Indian War, was head of the local militia and the Lower Regiment of Cumberland County, and led his men to fight with General Stark in the Battle of Bennington.

The Colonel and his wife and daughters did not live for long in the house, as it passed to Town Clerk William Mather in 1773, and subsequently to Captain Simeon Adams in 1783. Thereupon it stayed in the Adams family for four generations, being expanded with the addition of bedrooms and outbuildings as the family grew. It consisted of 600 acres, including a large sugar maple orchard. In 1896, it passed to the Eames family, who operated it as a dairy farm – 5 Maples Farm – into the 1940s.

Farming ended in 1945 when the Eames family sold it to H. Parks and Minnie Holcomb, who rented it as dorms and art department to newly opened Marlboro College. They also started selling off parcels of land, and tragically, cut down most of the 600 sugar maples and sold the wood. With the building of dormitories at the college, the trees gone, and the property shrunk, the Holcombs sold off the property in 1959.

Over the next couple years, it served as a rehabilitation facility for recovering alcoholics, who actually did much to restore the home, which had suffered over the years.

In 1961, the property began its new life as an inn, being purchased and renovated by Isobel Hartenbach, who named it Marlborough House. The Inn has continued to the present day under various owners, and under various names, until 1997 when it assumed the rightful name in honor of its original builder and owner, the estimable Colonel Williams.

One last note – a rather unpleasant ghost is said to haunt the Carriage House guest suite – a “perverted, homophobic, jerk”. Read more about this on the Colonel Williams Inn blog.

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