The Best of Route 7 | The Perfect Three-State Fall Foliage Drive

On this stunning fall foliage road trip from Vermont to Connecticut, there’s no shortage of great places to eat, stay, and play.

By Yankee Magazine

Aug 30 2022


Shelburne Museum

Photo Credit : Andy Duback

For the fall travel feature in Yankee’s September/October issue, “The Magnificent 7”, writer Alana Chernilla drove from Shelburne, Vermont, to Kent, Connecticut, along Route 7 — soaking up scenery and local flavor all along the 200-plus miles. If it inspires you to take a Route 7 road trip of your own this fall, here are our recommendations for the best stops along the way.

Shelburne to Rutland, VT | 60 miles

The Best of Route 7 | Shelburne Museum, Shelburne, VT
Photo Credit : Andy Duback


O Bread Bakery, Shelburne: Artisanal sourdough breads and sweet treats, all against the stunning backdrop of Shelburne Farms.

Rustic Roots, Shelburne: Bountiful and creative farm-to-table fare for breakfast and lunch. Reserve ahead for a sweet outdoor table.

Vermont Cookie Love, North Ferrisburgh: Come for the cookies, stay for the maple creamees, which are some of the best you’ll find.

Starry Night Café, Ferrisburgh: Local, organic, Vermont-focused food served in a stunning historic space filled with crafts by local artisans.

Bar Antidote, Vergennes: Locally sourced food and craft cocktails in a speakeasy-type setting.

Lincoln Peak Vineyard, New Haven: The only thing better than the views is the wine. Stop by for a curated wine flight and a local cheese plate.

American Flatbread, Middlebury: An ever-changing roster of Vermont craft beers with wood-fired pies topped with local ingredients.

Haymaker Bun Co., Middlebury: You may never go back to a familiar cinnamon bun after biting into Caroline Corrente’s unique creations on the banks of Otter Creek.

Cafe Provence, Brandon: Classic French food with a lovely outdoor seating area. The kind of place where people drink wine with lunch.


Shelburne Farms, Shelburne: An educational nonprofit on the site of a sweeping Vanderbilt estate. Explore endless trails, meet the animals, and visit the cheese room and bakery. Stay overnight in the historic waterside lodge.

Shelburne Museum, Shelburne: An experience of American history, culture, and design like no other.

Shelburne Farmers’ Market: Saturdays till mid-October. Local produce and meats, crafts, music.

Rokeby Museum, Ferrisburgh: A National Historic Landmark that’s one of the best-documented Underground Railroad sites in the country.

Monroe St. Books, Middlebury: This used bookstore right off Route 7 offers stacks and stacks of volumes to get lost in for hours.

Lake Dunmore, Salisbury: Rent a cabin on the lake, go camping at Branbury State Park, or hike the Silverlake trail.


Heart of the Village Inn, Shelburne: A sweet B&B right in downtown Shelburne.

Swift House Inn, Middlebury: A stunning hilltop house that offers the full Vermont experience. The bonus? There’s a fantastic restaurant onsite.

Rutland, VT, to the Berkshires | 68 miles


Zoey’s Double Hex, Manchester: A bustling and cozy local spot with phenomenal burgers and friendly service.

Blue Benn Diner, Bennington: A true institution that serves some of the best diner food in New England. Try the homemade doughnut grilled and topped with vanilla ice cream.


Rutland Murals: Let the map guide you on an ultimate townwide treasure hunt.

Hathaway Farm Corn Maze, Rutland: Even if you’ve never walked a corn maze, this is a great stop—and you’ll wonder why it took you so long.

Hildene, Manchester: Robert Tod Lincoln’s sweeping estate. The house is stunning, topped only by the gardens and the mountain views around it.

Shops at Manchester: If outlet shopping is your thing, Manchester offers one of the finest selections of outlets and independent boutiques around.

Northshire Bookstore, Manchester Center.  Simply one of the finest independent bookstores in New England.

Mount Equinox Skyline Drive, Sunderland: The foliage drive of your dreams. Wear extra layers, as you’re seemingly on top of the world when you reach the observation decks at the summit.

Robert Frost Stone House Museum, Sunderland: Frost lived in this small house next to an orchard when he wrote his favorite poem, and the spirit of those words infuse the home and property.

Bennington Battle Monument, Bennington: Vermont’s most popular historic site, this 306-foot monument was built to commemorate the 1777 Battle of Bennington.

Bennington Museum, Bennington: A museum dedicated to the art and history of the region, with the largest public collection of paintings by Grandma Moses.

Armstrong Farm, Pownal: Veggies, maple syrup, and pumpkins galore. Instagram


North Shire Lodge, Manchester: Newly remodeled rooms, breakfast in the pub, and views of the mountains on all sides. Book directly to get free breakfast.

The Inn at Manchester, Manchester: An upscale B&B with great breakfast, a pool, and a pub stocked with Vermont beers and spirits.

The Equinox Golf Resort & Spa, Manchester: A grand resort with activities ranging from falconry to off-roading and fly fishing.

Wilburton Inn, Manchester. Magnificent mountain-view setting with inn and pet-friendly cottages, all run by a unique family of artists, scholars, and farmers.

Arcady Mountain Motor Lodge, Sunderland: Simple, clean, comfortable, and cozy B&B motor lodge surrounded by nature.

Four Chimneys Inn, Bennington: Unique rooms in a historic mansion, and a cozy cocktail lounge for unwinding after the days’ adventures.

The Berkshires to the Litchfield Hills | 65 miles

The Best of Route 7 | The Red Lion Inn, Stockbridge, MA
Photo Credit : Corey Hendrickson


Mezze Bistro + Bar, Williamstown: The perfect balance of fancy and comfortable. Call ahead—depending on the day it might be burger night or a prix fixe menu.

Olde Forge Restaurant, Lanesborough: Cozy pub at the base of Greylock, with great wings and an impressive beer selection.

Proprietor’s Lodge, Pittsfield: Newly renovated, large-group-friendly restaurant that’s all about the setting on Lake Pontoosuc.

High Lawn Farm, Lee: Enjoy a towering ice cream cone while getting to know the cows that provided the main ingredient. The farm stand also carries a selection of High Lawn cheese and dairy products.

Once Upon a Table, Stockbridge: Now under new ownership, this tiny bistro has a delicious local menu and perfect date-night vibes.

Marjoram and Roux, Great Barrington: Great coffee, pastry, and ingredient-forward lunch options, right at the top of historic Railroad Street.

Bistro Box, Great Barrington: The roadside burger shack of your dreams. Be prepared to stand in line, as their bacon-jam burgers, truffle fries, and local shakes are always in high demand.

Roberto’s Pizza, Sheffield: Terrific brick-oven pizza and fresh salads. Sit inside or grab a picnic table out back.


Williams College Museum of Art, Williamstown: Free to the public and always featuring shows that push boundaries and inspire the imagination.

The Clark, Williamstown: A showcase for American and European art. The setting includes reflecting pools and foliage-filled walking trails.

Cricket Creek Farm, Williamstown: Artisan cheese, raw milk. Encourages visitors to walk the farm, see the animals and observe cheesemaking.

Sheep Hill, Williamstown: A former dairy farm open for hiking and picnicking, with exquisite views of the foliage around Mount Greylock.

Mount Greylock, Lanesborough: Hike one of the many stunning hikes that lead to the highest peak in the state, or take the winding auto road for a view above the clouds.

The Mount, Lenox: Edith Wharton’s Berkshire home. The gardens and wide back porch are perfect picnic spots, and there’s even live music if you time your visit right.

Norman Rockwell Museum, Stockbridge: Both the museum’s collection and curated shows are worth the visit. Be sure to head up the hill to visit Rockwell’s studio.

The Mohican History Walking Tour of Stockbridge: Learn about the Stockbridge Munsee indigenous inhabitants of the Berkshires and beyond, through this online walking tour of downtown Stockbridge.

Windy Hill Orchard, Great Barrington: A perfect spot for the apple-picking part of the drive. Grab cider doughnuts to snack on as you walk up to the orchard, too.

Monument Mountain, Great Barrington: A roughly two-hour, 3.8-mile round-trip hike that delivers great views from the rocky peak.

Great Barrington Farmers’ Market: Saturdays through November 12. Considered the best in the Berkshires.

Campo di Fiori, Sheffield: As much a garden center as it is a beautiful way of life. The space is impeccably designed, and you’ll leave with a plant or two as well as endless inspiration to take into your own home.

The Pass, Sheffield: The Berkshires have become a center for cannabis tourism, and The Pass, started by the owner of nearby Berkshire Mountain Distillers, is a favorite of many aficionados.

Bartholomew’s Cobble/Hurlburt Hill, Sheffield: A pretty family walk, with some of the most diverse flora in the area. Across the street is the entrance to the hill, which spans from woodland to grassy and leads to one of the area’s best foliage views.


The Guest House at Field Farm, Williamstown: Art-filled rooms set in amid of more than 300 acres of conservation land, with miles of trails and sweeping views of Mount Greylock.

Maple Terrace Motel, Williamstown: A rare budget find in the area, with clean rooms and a pool with a view.

Hotel on North, Pittsfield: A beautifully curated boutique hotel with an urban feel, right in the center of Pittsfield.

Red Lion Inn, Stockbridge: A legendary hotel for all the right reasons. Sip on cocktails on the massive porch, swim in the outdoor year-round heated pool, and find yourself a part of history at every corner.

The Briarcliff Motel, Great Barrington: A pet-friendly modern and fun roadside motel opposite Monument Mountain, complete with a massive fire pit where you can get to know your fellow travelers.

Litchfield Hills, CT

The Best of Route 7 | Falls Village Café, Falls Village, CT
Photo Credit : Corey Hendrickson


Falls Village Café, Falls Village: An expansive high-ceilinged café with something for everyone, right in the heart of the village.

RSVP, West Cornwall: A highly celebrated French BYOB bistro, with limited seating and a fixed-price menu. Call ahead to reserve. 860-672-7787

Wilson’s Bakery and Café, Kent: Great food, great mission: from-scratch breakfast and lunch that’s also an essential element of the recovery program at the High Watch addiction treatment center.


Furnace–Art on Paper Archive, Falls Village: A tiny gallery with big inspiration. Be sure to explore the drawers to see the works of past shows.

Calf + Clover Creamery, Cornwall Bridge: Farm stand with veggies, dairy, meats, and heavenly chocolate milk.

Downtown Kent: This little Connecticut town bustles on the weekends with great shops and lunch joints. Yankee called it New England’s best foliage town.

Kent Falls State Park, Kent: Bring a picnic, hike your way up the falls, and spend an afternoon marveling at the wonders of nature.


The Falls Village Inn, Falls Village: This historic inn was renovated in 2010, and every room, from the sheets to the wallpaper, has been meticulously crafted by renowned interior designer Bunny Williams.

Kingsley Tavern, Kent: Comfy upscale fresh and local pub food with great takes on classics like the french dip and shrimp and grits.

The Cozy Inn of Connecticut, Kent: A quiet and restorative farm-based B&B with a focus on sustainability. Kent Falls Brewing is also on-site.