Pownal Center, Vermont: 10 Scenic Short Road Trips Nearby

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10 Easy Road Trips From Pownal Center, Vermont (All Outside Bennington County)

If you’re based in or near Pownal Center, Vermont and you’ve already explored everything close to home, don’t worry. You’re actually in a perfect spot for quick out-of-county adventures into Massachusetts, New York, and other parts of Vermont. All of the ideas below are outside Bennington County, but still close enough for a fun day trip or relaxed weekend. Think covered bridges, farm stands, mountain views, classic New England towns, and a few surprises you might not expect. Let’s hit the road.

1. Williamstown, MA – Art, Trails, and a Classic College Town Vibe

Just across the state line in Berkshire County, Massachusetts, Williamstown feels like the “grown-up but still fun” cousin of a Vermont village. It’s about a 15–20 minute drive from Pownal Center, so it’s an easy first stop when you want to get out of the county without going far. Top things to do in Williamstown:
  • The Clark Art Institute – A world-class art museum tucked into rolling hills. You’ll find everything from Impressionist paintings to outdoor sculptures. Even if you’re not usually into art museums, the walking paths and views alone are worth it.
  • Walk the Williams College campus – Stroll past the brick buildings, green lawns, and mountain backdrops. It’s a great place to stretch your legs after the drive.
  • Hop on a nearby trail – Look for shorter walks like the Stone Hill trails behind The Clark for a mellow hike with great views.
If you like the idea of small-town charm mixed with brainy college-town energy, Williamstown should be high on your list.

2. North Adams, MA – Art in an Old Mill Town

Drive a little farther into Berkshire County and you’ll hit North Adams, another good out-of-county road trip from Pownal Center. It has an artsy, slightly quirky feel, thanks to the massive museum that put it on the map. Don’t miss in North Adams:
  • MASS MoCA (Massachusetts Museum of Contemporary Art) – Set in a huge old factory complex, this place is full of large-scale modern art. Some installations are so big you actually walk through them. Even if you’re not an “art person,” it’s fun, surprising, and very different from a typical museum.
  • Downtown murals and shops – Take a casual walk through town. There are colorful murals, indie shops, and little cafés where you can refuel with coffee or a snack.
Looking for a full-day combo? Pair Williamstown in the morning with North Adams in the afternoon for a perfect Berkshire County loop.

3. Shelburne Falls, MA – A Quirky Village on the Deerfield River

Head east into Franklin County, Massachusetts and you’ll find Shelburne Falls, a small town that punches way above its weight in charm. Plan about a 1 to 1.5 hour drive from Pownal Center, depending on your route. Highlights in Shelburne Falls:
  • Bridge of Flowers – An old trolley bridge turned into a lush flower garden. In warmer months, it’s packed with blooms. It feels a bit like walking through a dreamy backyard over the river.
  • Glacial Potholes – Natural rock formations carved by swirling water in the river. You can view them from above and see how the water has shaped the stone over thousands of years.
  • Small-town Main Street – Pop into local shops, grab ice cream, or sit with a coffee and people-watch.
Shelburne Falls feels like the kind of place you stumble on during a Sunday drive and keep coming back to.

4. Deerfield, MA – Step Back in Time in Historic Deerfield

Also in Franklin County, MA, Historic Deerfield is a great choice if you enjoy early American history or just love wandering pretty old streets. What to do in Deerfield:
  • Historic Deerfield village – This living history museum is made up of preserved homes from the 1700s and 1800s. You can tour several of them to see period furniture, old kitchens, and everyday objects from colonial life.
  • Walk the mile-long main street – Even if you don’t do guided tours, the street itself is gorgeous. Big shade trees, wide lawns, and classic New England architecture make for a very peaceful stroll.
If you’ve ever wished you could step into a history book—but without it feeling stuffy—Deerfield is a nice, laid-back way to do it.

5. Troy, NY – Farmers’ Market, River Views, and Old Brick Streets

Cross into Rensselaer County, New York and follow the Hudson River north. Within about an hour from Pownal Center, you can be in Troy, a small city that’s been quietly reinventing itself. Best bets in Troy:
  • Troy Waterfront Farmers’ Market – Held downtown (indoors in winter, outdoors in warmer months), this market is packed with local food, baked goods, crafts, and live music. It’s one of the most loved farmers’ markets in the region.
  • Walk the historic streets – Troy has tons of 19th-century brick buildings and a charming, slightly gritty feel. It’s a fun place for photography and wandering.
  • Hudson riverfront – Take a walk along the river, especially around sunset. The views of the water and bridges are a nice reward after a day of exploring.
If you’re craving something less “country” and more “small city,” Troy makes a solid day trip.

6. Grafton Lakes State Park, NY – Easy Nature Escape

Still in Rensselaer County, Grafton Lakes State Park is one of those spots locals love when they want to spend the day outside without driving deep into the Adirondacks. Why go to Grafton Lakes:
  • Swimming and beach time – In summer, there’s a sandy beach area along Long Pond. It’s a family-friendly place to swim, relax, and soak up the sun.
  • Hiking and paddling – Multiple ponds mean options for kayaking, canoeing, or just strolling the forest trails.
  • Snowy-season fun – In winter, the park is used for snowshoeing, cross-country skiing, and sometimes ice fishing, depending on conditions.
It’s an easy way to trade your usual Vermont views for a slightly different New York landscape—without a long drive.

7. Lake George, NY – Classic Adirondack Vacation Vibes

Drive north into Washington County, New York and a bit beyond, and you’ll reach the southern gateway to the Adirondacks: Lake George. It’s a bit farther from Pownal Center, so think of this as more of a full-day or weekend trip. What to do around Lake George:
  • Lake cruises – Hop on a sightseeing boat to enjoy the mountains from the water. Many cruises offer narration, so you’ll learn a bit of history while you’re at it.
  • Swimming and beaches – Public beach areas give you an easy way to cool off on a hot day.
  • Mini-golf, arcades, and shops – The village area has that classic old-school vacation feel: souvenir shops, ice cream stands, and enough mini-golf courses to keep kids happy for hours.
Yes, it can be touristy—but sometimes that’s exactly the mood you’re in.

8. Poultney & Lake St. Catherine, VT – A Quiet Lakeside Getaway

Head north into Rutland County, Vermont and you’ll find Poultney, a small town near Lake St. Catherine. This is a relaxing option if you want water, woods, and a slower pace. Ideas around Poultney and Lake St. Catherine:
  • Lake St. Catherine State Park – Go for a swim, have a picnic, or rent a boat. The lake is big enough to explore but still feels cozy compared to the huge ones.
  • Rail trail or backroad biking – The area has old rail trails and quiet roads for biking or walking.
  • Explore Poultney village – Grab a bite, check out local businesses, and enjoy the small-town feel.
If you like the idea of a “no-rush” lake day, this is an easy drive from Pownal Center that feels like a mini-vacation.

9. Brattleboro, VT – Artsy, Laid-Back, and Right on the River

In Windham County, Vermont, Brattleboro has a friendly, artsy vibe that’s drawn visitors for years. From Pownal Center, it’s a very doable drive down the southeastern side of the state. What makes Brattleboro fun:
  • Downtown shops and galleries – Bookstores, art galleries, natural food co-ops, and coffee shops line the main streets. It’s a great town for strolling and browsing.
  • Connecticut River views – Walk down near the water or drive over one of the bridges for great views of the river and hills.
  • Local events – Brattleboro often hosts festivals, gallery walks, and live music. Check the local calendar before you go and you might time your visit with something special.
This is a good choice if you want a mix of nature, culture, and good food—all in one compact, walkable town.

10. Woodstock, VT – Classic Postcard-Perfect Vermont

Finally, head toward Windsor County, Vermont and visit Woodstock, one of the state’s most photographed towns. If you’ve ever seen a picture of a covered bridge with a white church steeple and rolling hills, it might have been taken here. Why Woodstock is worth the drive:
  • Quaint village center – Boutique shops, cozy cafés, and historic inns line the streets. It’s the kind of place where you’ll want to slow down and just wander.
  • Woodstock’s covered bridges – Drive or walk across a few of them for that classic Vermont experience.
  • Marsh-Billings-Rockefeller National Historical Park – Offers estate grounds, carriage roads, and forest trails. It’s a beautiful place to walk and learn a bit about conservation history.
If you’re looking for a “this is what people imagine when they say Vermont” kind of day trip, Woodstock delivers.

Tips for Planning Your Pownal Center Road Trips

Here are a few quick pointers to make your out-of-county adventures smoother:
  • Check drive times – Some spots, like Williamstown, are super close. Others, like Lake George and Woodstock, make more sense as full-day or weekend trips.
  • Look up seasonal hours – Museums, boat tours, and even some parks may have limited hours in fall and winter.
  • Pack layers – Weather in this part of New England can change fast. A light jacket in the car is almost always a good idea.
If you’re like me, you might start with the quick trips—Williamstown, North Adams, Grafton Lakes—and then work your way out to the longer ones when you have more time.

Where Will You Go Next From Pownal Center?

Living near Pownal Center, Vermont means you’re surrounded by great places in every direction: the Berkshires, the Hudson River Valley, the Green Mountains, and beyond. And the best part? You don’t have to stay in your own county to enjoy them. Which of these 10 out-of-county road trips are you most excited to try first? Have you already visited any of these spots and discovered a hidden gem—a café, a trail, a lookout—that deserves a shout-out? Share your thoughts in the comments and pass this guide along to friends or family who are looking for new things to do near Pownal Center. The more ideas we swap, the better our next road trips will be.
Location: Georgetown, IN, USA

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