10 Unforgettable Short Road Trips from Pownal, Vermont

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10 Easy Road Trips From Pownal, Vermont: Fun Day Trips Just Over The County Line

Looking for things to do *near* Pownal, Vermont, but ready to get out of Bennington County for the day? You’re in the perfect spot. Pownal sits right in the southwest corner of Vermont, which means you can hop into New York, Massachusetts, or other Vermont counties in under an hour. Whether you’re visiting Pownal or you live here and feel like you’ve “done it all,” these short out-of-county road trips will give you fresh ideas without a long drive. All of these trips start from Pownal and head into nearby counties:
  • Berkshire County, MA
  • Franklin County, MA
  • Rensselaer County, NY
  • Washington County, NY
  • Rutland County, VT
  • Windham County, VT
  • Windsor County, VT

1. Williamstown, MA & The Clark Art Institute (Berkshire County)

If you only do one day trip from Pownal, make it Williamstown. It’s about a 15–20 minute drive south and feels like a classic New England college town wrapped in mountains. Why go:
  • The Clark Art Institute – A world-class art museum with paintings, sculpture, and rotating exhibits on a beautiful hilltop campus.
  • Easy walking around the village green, coffee shops, and bookstores.
  • Gorgeous mountain views in every direction.
I once went “just for an hour” to the Clark and stayed until closing. The galleries are calm and quiet, and then you walk outside and you’re in rolling fields with mountain views. It’s like stepping into a painting and then walking back out of it. Trip tips from Pownal:
  • Drive time: About 15–20 minutes.
  • Bring: Comfortable walking shoes and a light jacket; the galleries can be cool.
  • Perfect for: Art lovers, couples, and relaxed weekend afternoons.

2. MASS MoCA & Downtown North Adams, MA (Berkshire County)

Just a bit farther than Williamstown, North Adams is home to one of the largest contemporary art museums in the country: MASS MoCA. Why go:
  • MASS MoCA – Massive industrial mill buildings turned into bold, modern art spaces.
  • Outdoor courtyards, live music, and quirky installations.
  • Walkable downtown with cafes, local shops, and murals.
Even if you’re not usually “into” modern art, MASS MoCA has a way of surprising you. Some rooms feel like you’ve walked into a dream, others like a movie set. It’s very kid-friendly, too, because there’s so much space to wander. Trip tips from Pownal:
  • Drive time: Around 25–30 minutes.
  • Bring: A camera and maybe earplugs if you’re sensitive to sound—some exhibits get loud.
  • Perfect for: Rainy days, families, and anyone who wants a big-city art experience without the city traffic.

3. Mount Greylock State Reservation Scenic Drive (Berkshire County)

From Pownal, you see a lot of hills. But if you want the highest peak in Massachusetts, head to Mount Greylock, just east of Williamstown. Why go:
  • Scenic auto roads up to the summit (open seasonally).
  • Panoramic views of the Berkshires and southern Vermont.
  • Plenty of short hikes and overlooks along the way.
On a clear day, the summit view stretches for miles. You’ll see layers of blue and green ridges fading into the distance. It’s the kind of spot that makes you want to just stand still and breathe for a bit. Trip tips from Pownal:
  • Drive time: About 40–50 minutes to the summit area (depending on your route).
  • Bring: Layers, even in summer; it’s cooler at the top.
  • Perfect for: Leaf-peeping in fall, sunrise or sunset drives, and low-key hiking.

4. Troy, NY: Historic Streets & Hudson River Vibes (Rensselaer County)

If you’re craving a little city energy, head west to Troy, New York, on the Hudson River. It has a mix of history, college-town feel, and a growing food scene. Why go:
  • Beautiful 19th-century brick buildings and historic streets.
  • Waterfront views along the Hudson River.
  • Farmers market (one of the best in the region) on Saturdays, year-round.
It’s the kind of place where you can grab a coffee, wander old streets, and imagine what life was like 150 years ago—while still finding modern bakeries and breweries on every corner. Trip tips from Pownal:
  • Drive time: About 50–60 minutes.
  • Bring: Comfortable shoes—you’ll want to stroll for a while.
  • Perfect for: Foodies, architecture lovers, and weekend exploring.

5. Grafton Lakes State Park (Rensselaer County, NY)

If you’d rather trade brick streets for pine trees and water, head to Grafton Lakes State Park, northeast of Troy. Why go:
  • Swimming area with a sandy beach (seasonal).
  • Multiple lakes for paddling and fishing.
  • Easy walking trails and picnic spots among the trees.
It has that classic “state park summer” feel—cool water, picnic tables, and kids running around in flip-flops. In winter, there’s snowshoeing and cross-country skiing. Trip tips from Pownal:
  • Drive time: Roughly 1 hour–1 hour 15 minutes.
  • Bring: Swimsuit and towels in summer; warm layers and boots in winter.
  • Perfect for: Families, low-cost beach days, and outdoor picnics.

6. Lake George Village & Waterfront (Washington County access, NY)

While most people think of Lake George as being in Warren County, one of the easiest ways to reach the lake area from Pownal is to swing up through Washington County and aim for the southern end of the lake. Why go:
  • Classic lakeside town feel: ice cream, arcades, and boat tours.
  • Public beaches and waterfront parks.
  • Endless options for mini-golf, shopping, and casual dining.
If you grew up taking trips to the lake every summer, Lake George will feel very familiar—in a good way. It’s a little busy in peak season, but that’s part of the charm. Trip tips from Pownal:
  • Drive time: Around 1 hour 15–1 hour 30 minutes (depending on your exact route through Washington County).
  • Bring: Sunscreen, extra clothes for kids, and some cash for small attractions.
  • Perfect for: Summer day trips, multi-generational family outings.

7. Poultney & Lake St. Catherine State Park (Rutland County, VT)

Looking for a quieter Vermont lake experience outside Bennington County? Head north into Rutland County and visit Lake St. Catherine State Park near Poultney. Why go:
  • Sand beach and designated swim area.
  • Grassy picnic areas with shade trees.
  • Boat access for paddling or small motorboats.
It feels more laid-back than some of the bigger lakes. On a weekday, you might feel like you’ve scored your own private corner of Vermont. Trip tips from Pownal:
  • Drive time: About 1 hour 15 minutes.
  • Bring: Picnic supplies, lawn chairs, and maybe a float for the water.
  • Perfect for: Couples, quiet outdoor days, and unplugging from screens.

8. Rutland Downtown & Pine Hill Park Trails (Rutland County, VT)

If you want a mix of small-city energy and outdoor time, Rutland is a solid choice. Why go:
  • Walkable downtown with shops, restaurants, and murals.
  • Pine Hill Park – Miles of wooded trails right next to town for hiking or mountain biking.
  • Seasonal events and a farmers market.
You can spend the morning on the trails and then grab lunch and a coffee downtown afterward—no long drives in between. Trip tips from Pownal:
  • Drive time: Roughly 1 hour 20–1 hour 30 minutes.
  • Bring: Hiking shoes or a mountain bike if you have one.
  • Perfect for: Active travelers and anyone who likes to mix town and trail in one day.

9. Brattleboro, VT: Artsy River Town (Windham County)

Head southeast from Pownal into Windham County and you’ll eventually reach Brattleboro, one of Vermont’s most creative, free-spirited towns. Why go:
  • Busy downtown with bookstores, galleries, and local shops.
  • Views of the Connecticut River from various points around town.
  • Strong arts and music scene, plus frequent festivals and events.
It’s the sort of place where you might go in for a cup of coffee and end up chatting with a local artist about their latest project. The energy is friendly and a little quirky—in the best way. Trip tips from Pownal:
  • Drive time: Around 1 hour 15–1 hour 30 minutes.
  • Bring: An open mind and maybe an extra tote bag—there are lots of tempting shops.
  • Perfect for: Art lovers, weekend wanderers, and anyone who enjoys people-watching from a cafĂ© window.

10. Woodstock, VT & Quechee Gorge (Windsor County)

If you’re up for a slightly longer day trip from Pownal, heading northeast into Windsor County brings you to two of Vermont’s most famous spots: Woodstock and Quechee Gorge. Why go:
  • Woodstock – Classic village green, covered bridges, and charming shops.
  • Quechee Gorge – Often called “Vermont’s Little Grand Canyon,” with a dramatic river gorge and trails.
  • Plenty of photo-worthy spots and easy walks.
Standing on the bridge over Quechee Gorge and looking down at the rushing water far below is a “wow” moment, especially if you hit it on a bright fall day. Trip tips from Pownal:
  • Drive time: About 1 hour 45 minutes–2 hours (best as a full-day trip).
  • Bring: Good walking shoes and a charged phone for photos.
  • Perfect for: Scenic drives, first-time Vermont visitors, and romantic getaways.

How to Choose Your Perfect Day Trip From Pownal

Not sure where to start? Here’s a quick way to narrow it down:
  • Love art and culture? Try Williamstown & The Clark, MASS MoCA, or Brattleboro.
  • Want big views? Go for Mount Greylock or Quechee Gorge.
  • Traveling with kids? Lake George, Grafton Lakes, or Lake St. Catherine are great bets.
  • Craving a small-city vibe? Head to Troy or Rutland.
One of the best parts of using Pownal as your base is how many different experiences you can reach in under two hours—art museums, mountain summits, lakes, and historic towns are all within easy driving distance.

Share Your Favorite Road Trips From Pownal

Have you taken a great day trip from Pownal into Massachusetts, New York, or another Vermont county?
  • Which spots did you love most?
  • Any hidden gems in Berkshire, Rensselaer, Washington, Rutland, Windham, Franklin, or Windsor Counties that others should know about?
Drop your ideas and stories in the comments so fellow travelers can discover new places too. And if you found this guide helpful, please share it with friends or family planning a visit to southern Vermont—your share might inspire someone’s next favorite road trip.
Location: Georgetown, IN, USA

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