Weekend Getaway: Explore Vermont’s Only National Scenic Byway
Note: We earn a commission from affiliate links that may be included in this post.
Did you know the Connecticut River Byway is the only National Scenic Byway in Vermont?
This 500-mile, three-stay byway spans the west and east shores of the Connecticut River, beginning in Massachusetts and traveling north through Vermont and New Hampshire to the Canadian border.
A journey on this meandering stretch of pavement includes far-reaching river views, historic river towns and cities, and acres of fertile farmland.
We recommend taking a weekend trip and driving 128 miles on Route 5 from Brattleboro to St. Johnsbury, Vermont, but of course, you can drive all the way to Canada if you have time.
The Connecticut River Byway is one of the most scenic drives in Vermont, and there are ample opportunities to extend your vacation.
Here’s a perfect three-day itinerary on the Connecticut River Byway in Vermont, best enjoyed between late May and late October.
Day One: Explore Brattleboro
Total driving time: Depends on where you’re coming from.
There’s only one Brattleboro in this big wide world, and it’s tucked away in southeastern Vermont. With just over 12,000 residents, Brattleboro is a small town with a distinctive urban flair.
The Abenaki people called the area Wantastiquet, which means ‘Lost River,’ ‘River of the Lonely Way,’ or ‘River that Leads West.’ The town was chartered as Brattleborough in 1753 and grew up as a mill town before becoming a vibrant commerce hub.
Modern-day Brattleboro is an oasis of art galleries, music venues, boutique shopping, and farm-to-table restaurants.
Here’s how to spend a perfect day in Brattleboro, Vermont.
Coffee and pastries at Fire Arts Cafe
Fire Arts Cafe is a stunning bakery and coffee shop where you can start your morning with a buttery croissant and a rich maple latte. Or maybe a slice of quiche and a steaming mug of tea. Decisions, decisions!
When you’ve had your caffeine fix and your fill of flaky pastries, head next door to Fire Arts Vermont, a combination glass-blowing and ceramics studio with a beautiful gallery featuring a colorful mix of ceramics and glass art.
Meet the Animals at Retreat Farm
Retreat Farm is a gorgeous property that is free to visit every day from dawn to dusk.
In addition to the myriad of special events offered throughout the year, you can stop by to watch frolicking goats and baby calves, explore the expansive gardens, hike the nature trails, or enjoy the forest playground.
This sprawling historic farm is a wonderful spot for peaceful reflection, connecting with the land, and learning more about sustainable practices. It’s one of our favorite spots to enjoy when visiting Brattleboro.
Lunch at Yalla
This wonderfully addictive little eatery is one of the reasons I make the drive to Brattleboro over and over again.
Serving Eastern Mediterranean specialties like falafel, hummus, homemade pitas, and a bunch of other delicacies, Yalla is one lunch spot that you absolutely have to put on your Brattleboro itinerary.
Yalla is open from Thursday to Sunday, between 11 am and 3 pm. It’s worth planning your schedule around.
Meander around Downtown Brattleboro
Downtown Brattleboro bustles as if it were a much larger town, and there are so many cool shops and galleries to explore. Take the afternoon/evening to poke around in the shops — many are open late on the weekends.
Here are some of the fun shops that we love to explore whenever we visit Brattleboro.
- Everyone’s Books: This family-owned independent bookstore offers a broad range of titles but specializes in books about the environment and social change.
- Twice Upon a Time: Taking second hand to the next level, with three floors of vintage clothing, furniture, jewelry, tools, and collectibles.
- Penelope Wurr: A fun and quirky European gift shop featuring glassware, ornaments, hats, cards, and more.
- Altiplano: Based in Brattleboro and Lake Atitlan, Guatemala, Altiplano is a boutique that works with cooperative groups and small family businesses to create innovative clothing, jewelry, bags, and home decor while supporting indigenous communities and the environment.
- Turn it Up!: Specializing in new and used vinyl, CDs, DVDs, video games, and vintage memorabilia.
- Cara Wolff Jewelry: Handmade and hand-finished jewelry by artist Cara Wolff – created from natural and repurposed materials and inspired by the beauty of the natural world.
Check out the Brattleboro Museum and Art Center
Located in the middle of downtown, the Brattleboro Museum and Art Center, or BMAC, is an unforgettable addition to the wealth of artistry on display in Brattleboro.
The museum contains six galleries that rotate exhibits every few months, which means you can keep coming back to see new things every time you’re in town.
Admission to the museum is “pay-what-you-can”; a donation of $5-10 per person is recommended but not required.
Dinner at T.J. Buckley’s
Make reservations to dine in a 1925 Worcester Dining Car at T.J. Buckley’s. This intimate setting sets the stage for a five-star dining experience that you won’t soon forget. Chef Michael Fuller expertly prepares each meal in an open kitchen from the best of locally foraged and farmed ingredients.
The menu at T.J. Buckley’s changes weekly, but no matter what you order, this place is sure to impress and delight.
Spend the Night at the Latchis Hotel
The Latchis Hotel has been welcoming guests to its beautiful Art Deco hotel for 85 years, preserving the history and charm of a bygone era while providing guests with all the modern amenities and comforts you’ve come to expect.
Each historic room features unique decor and furnishings, a record player with access to a large vinyl library, and comfy beds with luxury linens. Choose between mountain or city views, or for more budget accommodations, forgo the view altogether.
Free coffee is available in the lobby, and downtown Brattleboro is right outside your door.
Connected to the Latchis Hotel, the Latchis Theatre opened in September 1938, just a day after the Great New England Hurricane ripped through Vermont.
There’s no doubt that movie dates hit differently at the Latchis Theatre, whether you’re catching a Hollywood blockbuster, an indie film, or a special event, so be sure to check out the line-up when you’re in town.
Read Next: 19 Spectacular Things to Do in Brattleboro, Vermont
Day 2: Discover Bellows Falls, Windsor, and White River Junction
Total driving time: 65 miles and less than two hours
Today, you’ll be heading north on Route 5 and exploring the towns of Bellows Falls, Windsor, and White River Junction, as well as a drive-up mountain summit, a beautiful covered bridge, and an outdoor sculpture garden.
Breakfast at The Works in Brattleboro
Before heading north, fuel up for the journey at The Works. This delightful bakery, cafe, and coffee shop on Main Street specializes in freshly baked bagels with Vermont-sourced cream cheese, but there is a huge menu to choose from.
The Works is a small New England chain dedicated to serving delicious, healthy meals at reasonable prices. They work to support local suppliers and buy sustainable products whenever possible.
Grab a grain bowl, an egg sandwich, or a smoothie, and prepare for a day of adventuring.
Grist Mill Museum in Bellows Falls
Drive north on Route 5 and park in downtown Bellows Falls to explore the downtown area on foot. Your first stop should be the old Grist Mill, just down the hill on Mill Street.
Built in 1831 by John Cary, this historic brick mill was once the heart of Bellows Falls’ grain trade, powered by the steady flow of water from the nearby canal.
At the time, Cary controlled all the water rights at the southern end of the canal, ensuring his mill thrived. In 1875, the Adams family took ownership, running operations until the mill finally fell silent in 1961.
Today, much of its original machinery—both hydraulic and later electric—remains remarkably intact, offering a glimpse into its industrious past.
Now home to the Bellows Falls Historical Society Museum, the mill welcomes visitors on the weekends between 11 am and 3 pm.
There’s a short trail beyond the mill leading to a labyrinth and beautiful Connecticut River views.
Grab Coffee and a snack at Flat Iron Cooperative in Bellows Falls
While you’re in Bellows Falls, be sure to stop at Flat Iron Cooperative for a specialty coffee drink or a savory croissant to fuel more adventures. My favorite is their chocolate orange chai latte. Cozy up in the cafe, or grab your coffee to go and explore downtown Bellows Falls.
Drive to the Top of Mount Ascutney
Built between 1935 and 1938, Mount Ascutney State Park was one of the very first state parks established in Vermont.
The mountain’s first hiking trail was created way before that — in 1825. It was the first organized mountain hiking trail in Vermont, and some accounts suggest it was the first in the country.
Today, hikers can scale the mountain from one of four trailheads, or they can explore a series of summit trails after driving up the 3.7-mile toll road.
After driving up the toll road (Mount Ascutney Parkway) to the parking lot near the summit of Mount Ascutney, you’ll be rewarded with stunning views of the green mountains.
Take any of the boulder-encrusted trails that meander around the summit, and you’ll find yourself in a dark, enchanting forest that smells like Christmas because of the abundance of spruce and fir trees.
For a 360° view of the Green Mountains and the White Mountains of New Hampshire, climb the 24.5-foot high observation tower. Interpretive signs name the distant peaks in all directions, and it’s a pretty good spot for a selfie.
Visit the Cornish-Windsor Covered Bridge
At 449.5′ long, the Cornish-Windsor Covered Bridge is the longest wooden covered bridge in Vermont and held the record for the longest two-span covered bridge in the world until 2008.
New Hampshire actually owns the bridge, along with every other bridge connecting it with Vermont. In fact, New Hampshire owns the whole Connecticut River, all the way to the low-water mark on the western bank.
I’ve explored many covered bridges in Vermont (admittedly, not very many in New Hampshire), and I think this one is the prettiest and the most unique. Park on the New Hampshire side for photos.
Read Next: Paddle the Connecticut River in Windsor, Vermont
Path of Life Sculpture Garden and Harpoon Brewery
The Path of Life Sculpture Garden at Artisans Park in Windsor is a beautiful, artistic journey from birth to death and beyond, spread out among 14 acres of pastoral land overlooking the river. 18 giant sculptures grace the grounds, all of them seamlessly integrated with the surrounding landscape.
Stop into Great River Outfitters and pay the admission ($6 for adults, $3 for kids) before stepping out to explore this beautiful outdoor sanctuary.
We visited Path of Life during the summer when the world was lush and green. As we meandered from birth to death, we found numerous spots to relax, meditate, or just enjoy the surroundings.
Next stop is Harpoon Brewery’s Taproom and Beer Garden (also in Artisans Park), featuring a great selection of craft beer, wine, and cider, plus handmade brewery pretzels and a casual food menu.
Harpoon Brewery is open seven days a week, and dogs are permitted on the outdoor patio.
Land in White River Junction
Continue on Route 5 to White River Junction, another historic river town with an eclectic downtown full of galleries, thrift stores, and restaurants. This is the perfect spot to and for the night.
Check into the Historic Hotel Coolidge before meandering around town.
If you’re lucky, you might be able to catch a show at Northern Stage during your visit. This professional theater company presents world-class theatrical productions and new works at The Barrette Center for the Arts in downtown White River Junction.
For dinner, you will want to eat at Tuckerbox (reservations suggested), a lavishly decorated restaurant serving authentic Turkish cuisine (breakfast, lunch, and dinner). Try a güveç (earthenware casserole), and don’t forget to save room for dessert!
Day 3: Explore Norwich to St. Johnsbury
Total Driving Time: 64 miles and less than two hours
Today, you’re driving from White River Junction to St. Johnsbury for the last leg of your road trip. You’ll eat iconic pastries, take a roadside hike to gorgeous views, and enjoy one of Vermont’s most unusual museums.
Fuel Up at King Arthur Baking
Follow Route 5 for five miles from White River Junction to Norwich for a culinary adventure at King Arthur Baking Company.
King Arthur Baking Company got its start more than 200 years ago as the first flour company in the United States. This is the spot to indulge in flaky pastries or almond cloud cookies before shopping the King Arthur store for all kinds of kitchen gadgets and goodies.
The bread here is amazing, too, and it’s worth grabbing a loaf to snack on during the next stop.
Hike the Palisades Trail in Fairlee
Located in Fairlee, Vermont, the Palisades Trail is a short/sweet hike up to a cliff overlooking the highway.
It’s not an all-day adventure kind of hike; it’s an “I’ve got a full day of driving, but I need to stretch my legs” kind of hike. We all need that once in a while.
It’s 2.2 miles round trip, steep at first, but then it levels out to lovely views of Fairlee and the mountains beyond.
The good: This is right off the road, so it’s a nice stop to stretch your legs and take in the views. There were mushrooms everywhere, and I thought the views were pretty incredible for such a short hike.
The bad: The highway noise is constant, and the parking and trailhead are not marked. AllTrails got me pretty close. I parked in the Fire Dept lot and walked along the side of the highway exit ramp until I spotted a red trail marker on a tree and a path leading into the woods. Roadside walking was very quick, and I didn’t see any cars.
Lunch at Broken Hearts Burger in Fairlee
Craving a classic smash burger with a side of onion rings? Want to sit outside and enjoy the sunshine? Broken Hearts Burger is a local favorite with a classic diner vibe, great service, and memorable burgers.
Explore the Fairbanks Museum and Planetarium in St. Johnsbury
Continue north on Route 5 through Bradford, Newbury, and Barnet — all wonderful towns with Connecticut River views. Eventually, you’ll arrive in St. Johnsbury, the shire town of Caledonia County.
This is the commercial center and largest town by population in the Northeast Kingdom.
One of the most incredible places in St. Johnsbury is the Fairbanks Museum and Planetarium, founded in 1889. Inside, you’ll find all sorts of wonders — mounted animals, artifacts, fossils, artistically displayed insects, and Vermont’s only public planetarium.
This gem of a museum should be on everyone’s Vermont itinerary, and it’s an essential stop on the Connecticut River Byway.
Where to Next?
To return the way you came, only faster, hop on Interstate 91 South. You can be back in Brattleboro in under two hours. Here are some other ideas:
- Explore Vermont’s Northeast Kingdom: Spend a few days discovering Vermont’s wild countryside. Look for moose, explore Brighton State Park, Lake Willoughby, and the Museum of Everyday Life.
- Drive the Kancamagus Highway in New Hampshire: Start your journey in Lincoln, New Hampshire (about an hour from St. J), and drive 35 miles east to North Conway on one of New Hampshire’s most scenic roads.
- Woodstock: Backtrack to White River Junction and head west to Woodstock, Vermont, one of the prettiest towns in the state.
Follow us on social media for more Vermont inspiration!
