10 Unforgettable Short Road Trips from Manchester Center, Vermont

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10 Easy Road Trips From Manchester Center, Vermont: Iconic Things To Do Nearby

Looking for fun day trips from Manchester Center, VT that get you out of Bennington County for a bit? You’re in luck. Within about 30–90 minutes, you can hit mountain views, farm stands, small cities, waterfalls, and classic New England villages in several nearby counties in Vermont, New York, and Massachusetts. These 10 short road trips are perfect if you’re based in or visiting Manchester Center and want to explore more of the region without spending hours in the car.

1. Explore Burlington’s Little Cousin: Rutland, VT (Rutland County)

Rutland flies under the radar, but it’s a great small-city escape about an hour north of Manchester Center. Why go: Walkable downtown, local food, and easy access to the mountains.
  • Stroll downtown Rutland’s public art and murals. The city has dozens of colorful murals and sculptures tucked around corners and alleyways.
  • Check out the Wonderfeet Kids’ Museum if you’re traveling with children. It’s small but very hands-on.
  • Shop and snack along Merchants Row and Center Street. Look for local coffee, bakeries, and Vermont-made gifts.
On one trip, I parked once and spent a whole afternoon just wandering from mural to mural, grabbing coffee and people‑watching. It felt like a mini city break without the traffic headaches. Approximate drive from Manchester Center: About 50–60 minutes.

2. Ride the Gondola & Hike at Killington Resort (Rutland County, VT)

Even if you’re not a skier, Killington makes for a fun road trip in every season.
  • In summer and fall, ride the K-1 Gondola to the summit. On a clear day, you can see for miles across the Green Mountains.
  • Try a short hike from the top. Even an easy trail gives you big views.
  • In winter, of course, there’s world‑class skiing and snowboarding.
If you’ve got kids (or adults) who get bored easily, this is a good pick. The gondola ride itself is an adventure, and you don’t have to commit to a long hike to enjoy the scenery. Approximate drive: About 1 hour 15 minutes.

3. Wander the Quechee Gorge & Village (Windsor County, VT)

Quechee Gorge is often called “Vermont’s Little Grand Canyon.” It’s one of the most iconic things to do near Manchester Center and makes an easy half‑day trip.
  • Walk across the bridge over Quechee Gorge and look down at the Ottauquechee River far below.
  • Take the short trail down to the bottom if you’re up for a moderate walk. It’s steep in places but not very long.
  • Browse the shops and snack spots in Quechee Gorge Village nearby.
I remember standing on the bridge and feeling that little flip in my stomach when I looked straight down. If you’re afraid of heights, you may end up doing the slow shuffle across—but the view is worth it. Approximate drive: About 1 hour 15–25 minutes.

4. Step Back in Time in Woodstock, VT (Windsor County)

If you picture a classic New England postcard—white church, village green, covered bridge—you’re probably picturing something like Woodstock.
  • Stroll the Downtown Woodstock shops and galleries around the village green.
  • Walk across the Middle Covered Bridge and take photos by the river.
  • Visit a nearby farm, like Billings Farm & Museum, for a taste of Vermont’s rural history.
Woodstock is a great pick if you like slow travel: browsing bookstores, finding a cozy café, and taking your time. It’s also beautiful in fall when the foliage lights up the hills. Approximate drive: Around 1 hour 15–30 minutes.

5. Ski, Hike, or Golf at Okemo Mountain Resort (Windsor County, VT)

Okemo in Ludlow is another four‑season favorite and a solid road trip if you like being active.
  • In winter, enjoy family‑friendly skiing and snowboarding with lots of groomed trails.
  • In summer, try the mountain coaster, hiking trails, or scenic chairlift rides.
  • Play a round at Okemo Valley Golf Club if you’re into golf.
Compared to some big Western resorts, Okemo feels manageable: big enough to be fun, small enough not to be overwhelming. Approximate drive: About 1 hour from Manchester Center.

6. Discover Revolutionary History at Bennington Battlefield… in New York (Rensselaer & Washington Counties, NY)

Here’s a fun twist: the famous Battle of Bennington didn’t actually happen in Bennington, Vermont. It took place just across the border in what’s now Walloomsac, New York, in Washington County, near the Rensselaer County line.
  • Visit the Bennington Battlefield State Historic Site to walk the grounds of this key Revolutionary War battle.
  • Read the interpretive signs and imagine what the fields looked like in 1777.
  • Enjoy peaceful country roads, old farmhouses, and scenic rolling hills on the drive in.
If you’re a history buff—or traveling with one—this is a must‑do. It’s also a nice break from the busier Vermont tourist spots. Approximate drive: About 40–50 minutes.

7. Enjoy a Lakeside Break in Lake Bomoseen & Castleton, VT (Rutland County)

Craving some water views? Head up to the Lake Bomoseen area in Castleton.
  • Relax at Bomoseen State Park, with its sandy beach and picnic areas.
  • Rent a kayak or canoe in season and paddle along the shoreline.
  • Explore the small college town of Castleton for a bite to eat.
On a hot summer day, this is the kind of spot where you might plan to stay for an hour and end up spending the whole afternoon on the beach. Approximate drive: Around 1 hour.

8. Drive to Massachusetts for Culture in North Adams (Berkshire County, MA)

Cross the state line into Western Massachusetts and discover an artsy little city surrounded by mountains.
  • Visit MASS MoCA (Massachusetts Museum of Contemporary Art), one of the largest contemporary art museums in the country, housed in a converted factory complex.
  • Wander the downtown streets of North Adams, with their mix of old brick buildings and quirky shops.
  • Pair your visit with a scenic drive over the Mohawk Trail (Route 2) if you’ve got the time.
Even if you’re “not an art person,” MASS MoCA is an experience. Some of the installations are huge—you don’t just look at them, you walk through them. Approximate drive: About 1 hour 15 minutes.

9. Hit the Trails & Museums in Pittsfield, MA (Berkshire County)

Pittsfield is the biggest city in the Berkshires, but it still has that laid‑back Western Mass vibe.
  • Visit the Berkshire Museum, which blends art, history, and science under one roof.
  • Head to nearby Pittsfield State Forest for hiking, scenic overlooks, and quiet woodland drives.
  • Explore downtown Pittsfield for local restaurants and shops.
If you want a mix of culture and nature in one day trip from Manchester Center, this is a solid option. Approximate drive: Around 1 hour 20–30 minutes.

10. Relax in Classic Brattleboro, VT (Windham County)

Brattleboro sits along the Connecticut River and has a funky, artsy small‑town feel that draws visitors all year.
  • Walk downtown Main Street and browse bookstores, galleries, and local craft shops.
  • Check out the riverfront area and watch the water roll by.
  • Grab lunch or dinner at one of the many independent cafés and restaurants.
Brattleboro is one of those places where it’s fun to just wander without much of a plan. You can go for the day and feel like you’ve stepped into a completely different scene from Manchester Center. Approximate drive: About 1 hour 15–30 minutes.

Tips for Planning Your Road Trips From Manchester Center

To make the most of these short road trips near Manchester Center, Vermont:
  • Check the seasons: Some attractions, like mountain coasters or gondolas, may be seasonal.
  • Watch the weather: Mountain views and gorges are best on clear days.
  • Layer up: Even in summer, higher elevations and lakeside spots can feel cooler than town.
  • Bring snacks and water: Some drives cut through rural areas with long stretches between stores.
If you plan it right, you can easily combine a couple of these ideas into one full‑day loop—say, Woodstock and Quechee, or Rutland and Lake Bomoseen.

What’s Your Favorite Day Trip From Manchester Center?

Have you tried any of these short road trips from Manchester Center, VT? Did I miss a favorite spot in Rutland, Windsor, Windham, Berkshire, Rensselaer, Franklin, or Washington County? I’d love to hear your stories and tips:
  • Which of these trips would you do first?
  • Do you prefer small towns, museums, lakes, or mountain views?
Please share your own ideas in the comments so other travelers can discover them too. And if you found this guide helpful, share it with a friend
Location: Georgetown, IN, USA

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