Weekend Road Trip on the Molly Stark Scenic Byway in Vermont (A 3-Day Itinerary)
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Few roads in Vermont carry as much history as Vermont Route 9.
The Molly Stark Scenic Byway runs 48 miles across the southern Green Mountains, connecting the arts hub of Brattleboro to the Revolutionary War town of Bennington, and the names attached to this stretch of Vermont read like a who’s who of American history. Ethan Allen. Robert Frost. Grandma Moses. General John Stark, whose wife Molly gave the road its name.
Throw in some spectacular mountain scenery, beautiful state parks, historic villages, and some of the best hiking in southern Vermont, and you’ve got the perfect weekend road trip for history and outdoor lovers.
And speaking of history, you may be wondering how the wife of a war hero got a road named after her (not to mention a park and a school). Molly Stark (née Elizabeth Paige) was the wife of General John Stark, who led a scrappy militia of New Hampshire colonials against a force of British redcoats, German Hessians, and Loyalist troops at the Battle of Bennington on August 16, 1777.
Before the fight, Stark reportedly told his men: “Tonight, the American flag flies over yonder hill, or Molly Stark sleeps a widow!”
The Americans won decisively, and the road that runs through this part of Vermont has carried her name ever since. Molly herself never set foot in Vermont; she was home raising 10 children and converting a barn into a field hospital, but she’s immortalized here all the same.
This itinerary covers the byway over a long weekend, moving from east to west, Brattleboro to Bennington. Feel free to flip it if you’re coming from the other direction.
At-A-Glance: Molly Stark Scenic Byway (Vermont Route 9)
Here’s a bite-sized snapshot of everything you need to know to plan your trip weekend getaway exploring Vermont Route 9.
When to Go: Mid-May through October
Time Frame: 3 Days will give you just enough time.
Where to Stay: The Historic Latchis Hotel in Brattleboro and South Shire: A Little Hotel in Bennington.
Camping: Fort Dummer State Park (Brattleboro), Molly Stark State Park (Wilmington), Woodford State Park (Woodford) have tent/RV sites without hookups and lean-tos.
How to Get There: Albany International Airport (ALB) in Albany, NY, is about an hour from Bennington. Bradley International Airport (BDL) in Windsor Locks, CT, is less than two hours from Brattleboro.
Day 1: Explore Brattleboro
Today is all about Brattleboro, one of Vermont’s most culturally vibrant towns. You won’t need your car much for exploring.
Brattleboro earns your attention before you ever get on the byway.
With just over 12,000 residents, it feels bigger, and more alive, than you’d expect. The town started as Fort Drummer, a frontier stockade built in 1724, and grew into a thriving mill town before becoming the eclectic, arts-forward community it is today.
Start your morning with a wander through downtown. Main Street feels like it belongs to a much larger city with independent bookstores, galleries, boutiques, and restaurants packed into a compact, walkable area.
If you’re a bookshop person, both Everyone’s Books and Brattleboro Books are worth a browse. The Latchis Theatre, a stunning 1938 Art Deco building with Greek murals painted across the ceiling, is worth stepping into just to look up.
Before lunch, walk or drive a short distance to the Creamery Covered Bridge, a bright red, perfectly preserved 1879 bridge, now open to pedestrians only. It’s right near the Brattleboro Farmers’ Market, which is worth a stop on Saturdays if your timing works out. The grassy area beside the bridge is a perfect spot for an impromptu picnic.
Lunch: Yalla
If there’s one restaurant that pulls me back to Brattleboro over and over again, it’s Yalla.
This wonderfully addictive little spot serves Eastern Mediterranean specialties: falafel, hummus, and homemade pitas, made with care and served without fuss. It’s a small menu done really well, with food you’ll be thinking about for the rest of your trip.
Afternoon: Retreat Farm
After lunch, head to Retreat Farm, a 500-acre gathering place on the edge of Brattleboro that has been part of the community since the 1830s.
Meander the walking trails, say hello to the farm animals, and admire the beautifully preserved historic buildings.
If you’re visiting on a Thursday evening in summer, the Food Truck Roundup is not to be missed: a lively outdoor event with a dozen-plus local vendors and live music. Leave the dogs at home for this one.
Even without the food trucks, Retreat Farm is a great afternoon stop: easy trails, friendly animals, and the sense of community that Brattleboro does so well.
Dinner: T.J. Buckley’s
T.J. Buckley’s is a Brattleboro institution; a tiny, intimate restaurant housed in a vintage diner car on Elliot Street that seats only a handful of people at a time. The menu is short, seasonal, and seriously good. Make reservation well in advance, and be prepared for an intimate experience.
Where to Stay in Brattleboro
The Latchis Hotel is the obvious choice if you want to walk to everything. it’s right on Main Street, shares a building with the Latchis Theatre, and has that same wonderful Greco-Deco character.
It’s pet-friendly and surprisingly affordable for what you get. Book it.
Explore More: Read our guide to exploring all of Brattleboro, Vermont
Day 2: Brattleboro to Bennington on the Molly Stark Scenic Byway
Today you’ll drive the byway from east to west, with stops at the overlook, Wilmington, and the mountains in between. Total drive time without stops: about an hour.
Morning: Head West on Route 9
Leave Brattleboro well-fed and unhurried. The byway climbs west from the Connecticut River Valley into the Green Mountains almost immediately, following Whetstone Brook up into the hills.
About 25 miles west of Brattleboro, the road crests at the Hogback Mountain Scenic Overlook in Marlboro, and on a clear day, the view will leave you breathless. Ridge after ridge of wooded mountains rolls south toward a hazy horizon, all the way to 3,489-foot Mount Greylock in Massachusetts.
This is the high point of the drive, and it’s worth every minute you spend here. On peak foliage weekends in October, this pullout sees up to 10,000 visitors; come on a weekday if you can.
The Hogback Country Store sits right at the overlook, with ice cream, Vermont maple syrup, cheese, fudge, and pay-per-view binoculars if you want to really lean into the view.
Three miles past the overlook, Molly Stark State Park is a natural stretch-your-legs stop.
The 1.8-mile loop trail to the fire tower on top of 2,415-foot Mount Olga is one of the easiest fire tower hikes in Vermont, and the views from the top are worth the modest effort. As someone who conquering a fear of heights, this was my first fire tower climb. I’m happy to say, I survived, and loved the view from the top!
Two camping loops with 23 sites and 11 lean-tos make this a good option if you’d like to sleep in the mountains tonight instead.
Lunch: Wilmington
Continue west into Wilmington, where Route 9 meets Route 100 in the broad Deerfield River Valley.
This classic Vermont crossroads village has more going on than its small size suggests, thanks in large part to its proximity to Mount Snow and Lake Whitingham.
For lunch, Dot’s Diner is a solid choice.
This beloved Wilmington institution nearly didn’t survive Hurricane Irene in 2011, and locals and visitors have been supporting it enthusiastically ever since. Classic diner fare, honest portions, and the kind of atmosphere that feels exactly right for a road trip lunch.
If the weather is good and you have time before or after lunch, it’s worth driving down to Lake Whitingham (Harriman Reservoir) for a look.
Eight miles long with 28 miles of undeveloped shoreline, the lake is gorgeous in any season, glassy and still in the morning, full of sailboats on windy afternoons, and absolutely spectacular during fall foliage.
Explore More: Read our guide to the most perfect things to do in Wilmington, Vermont
Afternoon: Into the Green Mountains
Past Wilmington, the byway swings west and climbs back into the mountains toward Woodford State Park, the highest state park campground in Vermont at 2,400 feet.
Even if you’re not camping, it’s worth a short stop to walk the 2.3-mile loop around Adams Reservoir, a quiet mountain lake surrounded by a dense mixed forest of spruce, fir, and birch.
Just past Woodford, Route 9 crosses the Appalachian Trail. If your legs are willing, the hike south from the road climbs 1.8 miles to the summit of Harmon Hill, with big views of Bennington and the surrounding valley. It starts steep and levels out, a satisfying afternoon hike before you descend into town.
From the AT crossing, the byway drops down the western slope of the Green Mountains into Bennington. The views open up as you descend, and the transition from dense mountain forest to the broad Vermont Valley is lovely.
Dinner: Bennington
Welcmoe to Bennington, my home town!
For dinner, Madison Brewing Company on Main Street is a reliable, welcoming choice with locally crafted beer, good burgers, vegetarian options, and a friendly atmosphere that’s hard to beat after a day of driving and hiking.
The beer menu rotates seasonally, but if Old 76 (an English Yorkshire-style ale) is on tap, get it.
Where to Stay in Bennington
The Four Chimneys Inn in Old Bennington is a gorgeoous old inn with beautifully appointed rooms, an exceptional breakfast, and walking distance to the historic sites you’ll be exploring tomorrow. If you’d rather be closer to downtown, South Shire on Elm Street offers nine lovely rooms in a Victorian home within walking distance of restaurants and shops.
Day 3: Explore More Bennington
Give Bennington the morning and early afternoon; there’s more here than most people expect.
Not only is Bennington is one of New England’s most historically significant towns, it’s also a real, working Vermont community of about 15,000 people, not a museum piece.
Old Bennington Historic District
Start in Old Bennington, a small community listed on the National Register of Historic Places. Park at the Bennington Battle Monument and meander on foot.
The monument is the tallest man-made structure in Vermont, 306 feet of dolomite stone built between 1887 and 1889 to commemorate the battle that helped turn the tide of the Revolutionary War.
Between May and October, you can ride an elevator 200 feet up to the observation deck for a three-state view. A gift shop at the base sells Revolutionary War-era books, gifts, and souvenirs.
From the monument, walk south on maple-lined Monument Avenue to the Old First Church, designed by Lavius Fillmore and built in 1805.
Behind it is the Bennington Centre Cemetery, Vermont’s oldest known cemetery, where five Vermont governors, Revolutionary War soldiers, and Robert Frost are all buried.
Frost’s epitaph reads: “I had a lover’s quarrel with the world.” His wife Elinor, who died in 1938 while the family lived in nearby Shaftsbury, is buried beside him. Follow the signs; it’s easy to find.
The homes along Monument Avenue date from the late 1700s and are remarkably well preserved. Across from the church, the Walloomsac Inn, currently being restored, was built in 1771. Thomas Jefferson and James Madison both slept there in 1791.
Bennington Museum
Head down the hill to the Bennington Museum, which is one of the best small museums in Vermont.
The collection includes the world’s largest public collection of Grandma Moses paintings. Anna Mary Robertson Moses grew up just over the border in New York, took up painting at 76, and achieved remarkable critical success before her death at 101 in 1961.
The museum also holds the Bennington Battle Flag from 1776, believed to be the oldest Stars and Stripes in existence.
Museum Hours (June–October): Open daily except Wednesday, 10 am to 4 pm.
Lunch: Blue Benn Diner
For lunch, stop at the Blue Benn Diner on North Street. It’s a genuine 1957 Silk City diner car with jukeboxes on every table, classic diner fare, and a few eclectic surprises on the menu.
Open from 6 am to 3 pm Tuesday through Wednesday and Saturday through Sunday, and until 8 pm Thursday and Friday.
Before You Go: Bennington’s Covered Bridges
If you have time on your way out of town, Route 67A off Route 7A takes you past three covered bridges in Bennington and North Bennington: the Silk Road Bridge (1840), Paper Mill Village Bridge, and Burt Henry Bridge, all crossing the Walloomsac River within a few miles of each other.
Explore More: Read our complete guide to exploring Bennington, Vermont
Molly Stark Scenic Byway FAQs
Should I drive Route 9 from east to west or west to east?
Both directions work well. If you’re coming from Boston or the Connecticut River Valley on I-91, starting in Brattleboro and driving west is the natural choice. If you’re flying into Albany, start in Bennington and head east. The scenery rewards you equally in both directions; it really comes down to where you want to spend your first night.
When is the best time to drive the Molly Stark Scenic Byway?
Early to mid-October for fall foliage. This is one of the most beautiful stretches of road in southern Vermont during peak color season. Summer is ideal for camping, hiking, and swimming. The road is open and well-maintained year-round, but use extra care on the mountain sections in winter.
Is there cell service along Route 9?
It gets spotty in the mountain sections between Brattleboro and Wilmington. Download your maps offline before you leave, and consider picking up a DeLorme Vermont Atlas if you like a paper backup. The drive is well-signed, but peace of mind goes a long way in the mountains.
Can I combine this with other Vermont road trips?
Absolutely. From Bennington, head north on Historic Route 7 through Arlington and Manchester all the way to Burliington, a natural extension if you have more time. From Brattleboro, the Connecticut River Byway stretches north along the Vermont-New Hampshire border and is worth exploring in its own right.
Is this a good road trip for families?
Yes! Retreat Farm is wonderful for kids, Molly Stark State Park is easy and fun, and Woodford State Park’s lake and beach give everyone room to breathe. The drive itself is short enough that young travelers won’t run out of patience.
Are there places to eat along the way?
Brattleboro and Bennington both have full restaurant scenes. Wilmington has a handful of solid options thanks to the Mount Snow crowd. In between, services are limited; the Hogback Country Store at the overlook and the Vermont Country Deli near West Brattleboro are your best bets in the middle stretch.
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