10 Easy Out-of-County Road Trips From Stamford, Vermont
If you live in or around
Stamford, Vermont in Bennington County, you know it’s quiet, pretty, and a little off the beaten path. But sometimes you just want to hop in the car, roll down the windows, and find something new to do without driving all day.
That’s where these
short road trips from Stamford, VT come in.
All of these ideas are
out of Bennington County, in nearby counties across Vermont, Massachusetts, and New York:
- Berkshire County, MA
- Franklin County, MA
- Rensselaer County, NY
- Washington County, NY
- Rutland County, VT
- Windham County, VT
- Windsor County, VT
Most are within 30 minutes to 2 hours of Stamford, so they make great
day trips or easy weekend getaways.
1. Explore Art & Food in North Adams, MA (Berkshire County)
Just a short drive south over the state line,
North Adams, Massachusetts feels like a small city wrapped in mountains.
Why go: It’s a fun mix of art, history, and small-town charm.
- Visit the massive contemporary art museum at MASS MoCA (Massachusetts Museum of Contemporary Art). Even if you’re not a big “museum person,” the huge installations and old factory buildings are pretty cool to walk through.
- Stroll around downtown for coffee shops, local restaurants, and quirky galleries.
- Check out seasonal events and outdoor concerts—perfect for a casual date night or family outing.
From Stamford, it’s close enough that you can leave after breakfast and be home before dark, even after dinner in town.
2. Hike the High Peaks at Mount Greylock, MA (Berkshire County)
If you look south on a clear day, there’s a good chance you’re seeing
Mount Greylock, the highest point in Massachusetts.
What to do there:
- Drive the scenic road up to the summit in season, then walk to the War Memorial Tower for sweeping views across five states.
- Try an easy hike like the Veterans War Memorial Trail or pick a longer loop if you’re feeling adventurous.
- Pack a picnic and enjoy the cooler air at the top.
On my first trip there, I remember stepping out of the car at the summit and being hit with that crisp mountaintop breeze. It felt like I’d driven hours into the wilderness—but it was really just a short day trip from southern Vermont.
3. College-Town Vibes in Williamstown, MA (Berkshire County)
Another great stop in Berkshire County is
Williamstown, a classic New England college town.
Highlights:
- The Clark Art Institute – A world-class art museum with a peaceful campus and walking trails.
- A walk through the Williams College campus – Beautiful buildings, open lawns, and a relaxed vibe.
- Small-town main street – Cafés, bookstores, and local shops that are fun to wander through.
Williamstown is a nice choice if you want something low-key: a little culture, a little walking, and a good lunch before heading back to Stamford.
4. Shop, Dine, and Catch a Show in Pittsfield, MA (Berkshire County)
If you’re looking for more of a “small city” feel, head to
Pittsfield in Berkshire County.
Things to do:
- See a performance at the Barrington Stage Company or the Colonial Theatre.
- Visit Berkshire Museum for a mix of art, history, and science exhibits—great if you’ve got kids with you.
- Enjoy a night out at one of the local breweries or restaurants.
This is a good trip if someone in your group wants more buzz and nightlife than you’ll find in a smaller Vermont town.
5. History & River Views in Bennington, NY & Hoosick Falls, NY (Rensselaer County Area)
Crossing over into New York opens up another set of easy
road trips from Stamford, Vermont. In and around
Rensselaer County, you’ll find old mills, farms, and classic small towns.
Try a loop through the
Hoosick and
Bennington, NY area:
- Walk through historic villages with old churches and brick buildings.
- Explore small antique shops and roadside farm stands along the way.
- Stop by local diners or family-run restaurants for a simple, hearty meal.
This is one of those drives where the journey is half the fun—rolling hills, open fields, and big-sky views that feel a world away from your driveway in Stamford, even though you’re really not that far.
6. Riverfront Walks and History in Troy, NY (Rensselaer County)
Troy, New York sits along the Hudson River and has a lot of character: old brick warehouses, historic streets, and a growing food scene.
What to check out:
- Stroll the waterfront and enjoy views of the river.
- Browse the Saturday farmers’ market (seasonal) for local produce, baked goods, and crafts.
- Walk around the historic downtown, with its 19th-century architecture and cool side streets.
If you’re craving something different from the mountains and forests of Vermont, a day in Troy gives you more of an urban feel—without the stress of a huge city.
7. Farm Country & Lakes in Washington County, NY
Drive a little farther north and west, and you’ll hit
Washington County, New York, a scenic mix of farmland, lakes, and small villages.
You can easily build a relaxed day here:
- Take a lazy drive through back roads lined with barns and rolling pastures.
- Check out lakes like Lake Lauderdale or other small local spots for swimming, paddling, or just a picnic by the water.
- Visit farm stands for fresh veggies, eggs, maple syrup, and homemade baked goods.
If you love photography, this entire area is basically one big postcard—especially in fall when the leaves turn. It’s an ideal low-stress escape from everyday routines in Stamford.
8. Outdoor Adventures around Rutland, VT (Rutland County)
To the north,
Rutland County offers a lot for outdoor lovers, and you don’t have to be an athlete to enjoy it.
Around the
Rutland area you can:
- Bike or walk along sections of the Delaware & Hudson Rail Trail or local paved bike paths.
- Visit nearby lakes for swimming, kayaking, or stand-up paddleboarding in summer.
- Explore downtown Rutland’s murals and small shops when you’re ready for a snack or coffee.
In winter, this is also a good jumping-off point for ski areas in central Vermont if you want to make it a full weekend getaway.
9. Scenic Drives & Covered Bridges in Windham County, VT
Head east from Stamford and you’ll land in
Windham County, Vermont, home to classic small towns and beautiful back roads.
Ideas for your day:
- Drive through villages like Newfane or Townshend with picture-perfect town greens and white church steeples.
- Hunt for covered bridges and pull over for photos.
- Stop for homemade ice cream, local cheeses, or maple products at roadside spots.
If you enjoy aimless Sunday drives, this area is hard to beat. You don’t need a strict plan—just pick a direction, bring snacks, and see where the road takes you.
10. Classic Vermont Charm in Woodstock & Quechee, VT (Windsor County)
Windsor County is home to some of Vermont’s most iconic small towns, and it’s absolutely worth a day trip from Stamford.
Focus on the
Woodstock–Quechee area:
- Walk around Woodstock, with its charming downtown, historic homes, and covered bridge.
- Visit Quechee Gorge, sometimes called “Vermont’s Little Grand Canyon.” You can walk across the bridge for a dramatic view and hike down to the bottom if you’re up for it.
- Check out local shops selling Vermont-made products: maple syrup, cheese, crafts, and more.
This is a great choice for out-of-town visitors: you get the “classic Vermont” experience in one easy trip.
Tips for Planning Your Stamford, VT Road Trips
To make the most of these
day trips from Stamford, Vermont:
- Check drive times: Most of these spots are within 30–120 minutes. That keeps your day fun instead of tiring.
- Watch the seasons: Fall foliage, summer lakes, winter skiing, and spring maple season each offer something different.
- Bring layers: Mountain weather can change fast, even if it feels warm when you leave Stamford.
- Pack simple snacks and water: Handy for hikes, scenic overlooks, or long photo stops.
You don’t need a huge budget or a long vacation to feel like you’ve gone somewhere new. Sometimes a one-hour drive is enough to reset your mind.
Share Your Favorite Stamford, VT Road Trip Ideas
Now it’s your turn.
- Have you tried any of these road trips from Stamford, Vermont?
- Do you have a favorite hidden spot in Berkshire County, Rutland County, or across the border in New York?
Drop your experiences and tips in the comments to help other travelers plan their own adventures.
And if you know someone living near Stamford who’s always saying, “There’s nothing to do around here,” send them this post. Sometimes all you need is a full gas tank, a good playlist, and a rough idea of which direction to drive.
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