10 Best Things To Do Near Pownal, Vermont (Bennington County)

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10 Relaxing Things To Do Near Pownal, Vermont (Bennington County)

Looking for a quiet, off-the-beaten-path Vermont escape? Pownal, Vermont, tucked in the southern tip of Bennington County, is one of those small towns you can blink and miss from the highway—but you definitely shouldn’t. If you love scenic drives, farm stands, country roads, and easy outdoor adventures, this corner of southern Vermont is a great base. You’re close to Vermont, Massachusetts, and New York all at once, which means lots of options within a short drive. Below are 10 things to do in and around Pownal, VT that make for a relaxing, low-key New England getaway.

1. Take the Classic Vermont Drive Along Route 7

One of the simplest pleasures near Pownal is just… driving. Vermont Route 7 runs right through town and is one of the prettiest drives in southern Vermont. The rolling hills, farm fields, and mountain views make even a quick trip to the store feel like a scenic tour.
  • Head north toward Bennington for views of the Green Mountains.
  • Drive south into Massachusetts for more open farmland and valley views.
If you can, time your visit for:
  • Early October for peak fall foliage, when the hills look like they’re on fire with reds and golds.
  • Late afternoon in summer for that golden-hour glow on the barns and fields.
I once pulled over at a random farm pull-off south of Pownal just to snap a photo, and ended up staying 20 minutes just watching clouds roll over the hills. It’s that kind of place.

2. Explore Downtown Bennington

Just about a 20–25 minute drive north from Pownal, Bennington, VT is your go-to “small city” in the area. It’s big enough to have great food and shops, but still feels cozy and local. Stroll through:
  • Downtown Bennington – Local shops, art galleries, and cafés along Main Street.
  • Bennington Battle Monument – A massive stone monument you can see from far away. You can ride an elevator to the top for a wide view over Vermont, New York, and Massachusetts.
  • Bennington Museum – Regional history and art, including works by Grandma Moses.
If you’re staying in or near Pownal, Bennington is where you’ll likely:
  • Grab a sit-down meal.
  • Pick up groceries or snacks.
  • Stretch your legs on an easy town walk.
It pairs perfectly with a quiet base back in Pownal.

3. Visit an Old-School Vermont Farm Stand

Vermont is known for its small farms, and the Pownal area is no exception. While some stands are seasonal and can change year to year, keep an eye out as you drive through town and along Route 7. You might find:
  • Fresh veggies in summer—corn, tomatoes, zucchini, and more.
  • Apples, cider, and maple products in the fall.
  • Local eggs, jams, and baked goods from nearby farms.
These farm stands are often simple—sometimes just a small shed or table with a cash box. That “honor system” setup is part of the charm. Tip: If you see a hand-painted sign for maple syrup along a side road, follow it. That’s how many people discover their favorite little Vermont spot.

4. Hike (or Stroll) in the Green Mountains

You don’t have to be a hard-core hiker to enjoy the Green Mountains near Pownal. There are trails for all levels within a short drive. A few ideas in the Bennington area:
  • Hiking near the Bennington Battle Monument – Short paths and viewpoints around town and along nearby roads.
  • Local forest roads and short woods walks – Many side roads off Route 7 lead to state forests or quiet walking areas.
If you’re open to driving a bit farther:
  • Glastenbury and surrounding forest areas offer deeper woods and longer hikes.
Always check:
  • Local maps or visitor information in Bennington.
  • Trail conditions, especially in early spring and late fall.
Even a simple 30-minute walk on a forest trail near Pownal can feel like a reset button for your brain.

5. Enjoy a Peaceful Country Stay

One of the best “activities” near Pownal is simply staying put. This part of southern Vermont is dotted with:
  • Small inns and bed-and-breakfasts.
  • Cabins and cottages.
  • Farm stays and vacation rentals.
What makes it special?
  • Dark skies at night for stargazing.
  • Quiet mornings with misty hills and coffee on the porch.
  • Cool evenings even in mid-summer, thanks to the higher elevation.
If you’re coming from a busy city, it can feel almost unreal to hear nothing but crickets and the wind at night.

6. Take a Day Trip to Williamstown, Massachusetts

Just over the state line, about a 15-minute drive south from Pownal, is Williamstown, MA, a charming college town that’s perfect for a half-day visit. What to do there:
  • Williams College campus – Walk through the pretty New England campus with its brick buildings and green lawns.
  • Local cafés and bakeries – Great for a slow breakfast or an afternoon snack.
  • Art and culture – Williamstown is known for museums and theater, especially in summer.
This is a nice way to add a bit of “culture and coffee” to a mostly-nature-focused Pownal trip.

7. Chase Covered Bridges in Bennington County

If you picture Vermont in your mind, there’s probably a covered bridge in that image. The good news: you can see real ones within a short drive of Pownal. Near Bennington, look for:
  • Silk Road Covered Bridge
  • Paper Mill Village Bridge
  • Henry Covered Bridge
These classic wooden bridges cross the Walloomsac River and its branches. They’re great for:
  • Quick photo stops.
  • Short walks along the water.
  • Fall foliage shots if you visit in October.
It’s an easy “mini tour” from Pownal: drive up toward Bennington, loop across a few bridges, and head back via a different back road for new views.

8. Follow the Local Brewery and Cider Trail

Vermont takes its beer and cider seriously. While Pownal itself is tiny, the broader Bennington County area has spots where you can sample local drinks. Depending on what’s open when you visit, you can:
  • Try Vermont craft beers on tap in Bennington bars and restaurants.
  • Look for regional ciders made with local apples.
  • Pick up bottles or cans to enjoy back at your rental after a day of exploring.
If you’re not a drinker, many places also offer:
  • House-made sodas.
  • Local kombucha.
  • Non-alcoholic craft options.
Always remember to plan a safe ride and keep the driving separate from the tasting.

9. Experience Vermont’s Four Seasons

One of the best things about staying near Pownal is that it feels different in every season. You can visit the same places and get a totally new vibe. Here’s what to expect:
  • Spring (April–May)
    Melting snow, rushing streams, and the first pops of green. It’s also mud season, so bring boots if you’re heading onto trails.
  • Summer (June–August)
    Warm days, cooler nights, and great driving weather. Farm stands and outdoor dining start to pick up.
  • Fall (late September–mid-October)
    This is the showstopper. Hillsides explode with color, and scenic drives around Pownal and Bennington are unforgettable.
  • Winter (December–February)
    Quiet, peaceful, and often snowy. Ideal if you like cozy cabins, wood stoves, and uncrowded roads—just be sure your vehicle is ready for winter driving.
If you’ve only seen Vermont in summer, consider coming back in fall or winter for a totally different experience.

10. Slow Down and Savor Small-Town Vermont

Finally, one of the top “things to do” near Pownal is simply to slow down and let the small-town rhythm sink in. A few simple pleasures:
  • Grab coffee in Bennington and take the long way back to Pownal.
  • Pull over at a scenic overlook and just sit for a few minutes.
  • Watch the fog roll through the valley early in the morning.
  • Sit outside at night and count how many stars you can see.
In a world that’s always rushing, this corner of Bennington County, Vermont invites you to move at a different pace. It’s less about big attractions and more about small, quiet moments.

Planning Your Trip to Pownal, Vermont

To make the most of your visit to Pownal and the surrounding area:
  • Have a car – This region is very drive-friendly, and most places are spread out.
  • Check seasonal hours – Many farm stands, shops, and attractions have different hours depending on the season.
  • Book lodging early for fall foliage – October weekends can fill up quickly across southern Vermont.
  • Pack layers – Even in summer, evenings can be cool in the hills.

Share Your Pownal, VT Experience

Have you been to Pownal or Bennington County? Did you discover a scenic back road, a favorite farm stand, or a cozy cabin stay?
  • Drop a comment and share your tips, stories, or questions about visiting Pownal, Vermont.
  • If you found this guide helpful, share it with a friend who loves road trips and small-town New England getaways.
Your experiences can help other travelers discover this quiet corner of southern Vermont—and maybe inspire their next peaceful escape.
Location: Georgetown, IN, USA

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