Southern Vermont. Pic: Shutterstock.

Best New England Road Trips: Southern Vermont

BY Rob LeDonne | August 28, 2020

Get ready to explore a majestic land of covered bridges, mountain vistas and family farms. Humbly nestled due north, the romanticism of Vermont has been an open secret for decades; so serene the area was  forever immortalized in the lush standard “Moonlight in Vermont” (made popular by both Frank Sinatra and Ella Fitzgerald). While many may think of Vermont (named for the French words for “green” and “mountain”) as a winter or fall destination for both skiing and leaf peeping, its idyllic countryside and quaint villages are just as viable and vibrant during as the sweltering summertime winds down.

In our current Covid-influenced era where nature-forward trips are ideal, make right now the time for a laid-back jaunt around southern Vermont that safely takes in all its glories. “Evening summer breeze, sweet warblings of the meadowlark,” as the song goes. “Moonlight in Vermont…” You could experience it, too.


Honeypie in Jamaica, Vermont.
Honeypie in Jamaica, Vermont.


8811 VT-30, Jamaica, VT, USA

This isn’t just any old roadside burger stand. A family-owned oasis for gourmet grub, it’s Honeypie’s attention to detail that makes it stand out brighter and bigger than any other burger spot that currently holds a place in your meaty heart. (I’m looking at you, Shake Shack.) Hawking burgers and fries that are hand-ground and hand-cut daily, as well as handmade sausage stuffed with regional stock (think delectable pork and lamb links), as well as shakes that are totally worth the however many calories they clock in at, Honeypie is next-level at every turn. Even better, its small digs (outfitted with an Instagramable sign!) are Covid-friendly: stand on a socially distanced line outside and enjoy your order laying out on the grass next door.

Dutton Farm
Dutton Farm

Dutton Farm Stand

2083 Depot St, Manchester Center, VT, USA

If there were ever a quintessential Vermont farm stand, Dutton comes pretty darn close. More of a farm “shack,” considering it’s housed in an equally expansive and weathered building, Dutton is like a Vermont fever dream. Think: multiple varieties of fresh maple syrup from dark to light, tons of recently picked fruits and vegetables, containers of fresh ooey-gooey honey, just-cut flowers, baked goods, and that’s just a small sampling. Also keep a sharp eye out for their very own Dutton’s Blend coffee, courtesy regional coffee roasters Pierce Bros. Whether you need a gift for a friend or want to treat yo’self, Dutton’s will make your local Vermont shopping dreams come to life. 



Northshire Bookstore

4869 Main St, Manchester Center, VT, USA

There’s nothing more relaxing on a quiet summer’s evening following a long day than curling up with a good book as the sun begins to hide behind the mountains ahead. Fortunately, tourists and locals alike have plenty to choose from at Manchester Center’s proudly independent Northshire Bookstore. Housed in a 10,000-square-foot, century-old inn and in continual operation since 1976, Northshire will make you leave Amazon in the dust thanks to its down-home quaintness and selection of gifts and stationery. Even better, the store is attached to the Bonnet & Main Cafe, which allows you to pick up both an iced coffee and the latest novel all in one trip. And for folks unable to get down to Vermont this summer, the bookstore is offering Covid-friendly digital events, including talks with bestselling authors via their website.


Vermont cheese! Photo from Shutterstock
Vermont cheese! Photo from Shutterstock

Taylor Farm

825 VT-11, Londonderry, VT, USA

Have you ever wanted to meet a pig? How about a rooster? Then take a walk on the wild side around the family-owned Taylor Farm, which allows you to get up close and personal with the animals who call the actual working farm home sweet home. From its pen full of hefty oinkers, stable of friendly horses and tons of chickens and roosters that mosey around, it’ll whet your craving for some animal-friendly fun surrounded by picturesque settings, like classic red barns and grassy expanses. Even better, the Londonderry farm has events year-round, from live music under the stars to cookouts and sleigh rides. Giddy up, indeed.


Great River Outfitters via
Great River Outfitters via

Great River Outfitters

36 Park Rd, Windsor, VT, USA

Picture this: You’re floating idly down a calm river in the midday sun with your feet in the cool water and your mind on nothing but nature and the refreshing drink in your hand. If this sounds like paradise, you can thank Windsor’s Great River Outfitters, considering it’s your one-stop shop for aquatic adventures down the Connecticut river. Whether tubing, rafting or canoeing, Great River has you covered. Just arrive at their lodge and they’ll bus you five miles upriver so you can take your sweet time coming back down. It’s summer in Vermont at its finest that boasts ideal activities during these socially distant times. 


Harpoon Brewery Riverbend Taps and Beer Garden
Harpoon Brewery Riverbend Taps and Beer Garden. Photo courtesy of

Harpoon Brewery Riverbend Taps and Beer Garden

336 Ruth Carney Drive, Windsor, VT, USA

Right next door to Great River Outfitters’ headquarters is this brewery and outdoor beer garden for Harpoon, a Boston-based beermaker known for its frothy India Pale Ales and Hefeweizen. With wide open spaces (it’s well known for its Oktoberfest bash, as well as the brewery-eponymous Harpoonfest), it’s the perfect outside activity to spread out and guzzle down a beer, hard cider or hard seltzer. Call ahead though, because as capacity is limited reservations could be required. 


View of mountains in Vermont from Mount Equinox. Pic: Shutterstock
View of mountains in Vermont from Mount Equinox. Pic: Shutterstock

Equinox Mountain

Skyline Dr, Sunderland, VT, USA

Now that you’ve taken in Vermont and its charms and fully understand what Frank and Ella were singing about, go the distance and feast your eyes on the astounding geography the state has to offer atop Equinox Mountain. The highest mountain in southern Vermont (elevation: 3,848) is chock-full of hiking trails, along with a lodge they dub the Saint Bruno Scenic Viewing Center, which not only offers views of the Green Mountain State, but glimpses at the mountains in nearby New York, Massachusetts and New Hampshire.