10 Unforgettable Short Road Trips From Rutland, Vermont

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10 Easy Road Trips From Rutland, VT: Fun Things To Do Just Outside Rutland County

Are you based in Rutland, Vermont and itching to hit the road for a few hours? Maybe you’ve already done all the usual downtown Rutland spots and hikes, and now you’re wondering, “What’s next?” Good news: you don’t have to drive far to find new adventures. Within about an hour or so, you can explore charming towns, covered bridges, mountain views, local food, and some of the most classic Vermont scenery around—without leaving the region. Below are 10 easy out-of-county road trip ideas from Rutland into the nearby counties of Addison, Bennington, Windsor in Vermont and Washington County, New York. Each one is perfect for a day trip or a slow weekend getaway.

1. Middlebury, VT – College Town Charm & Waterfall Views (Addison County)

Drive time from Rutland: about 45–60 minutes Middlebury feels like the classic Vermont town you see on postcards. It’s a small college town with brick buildings, a river running right through downtown, and a laid-back vibe. Things to do in Middlebury:
  • Stroll downtown Middlebury – Check out local shops, bookstores, and cafés along Main Street.
  • See the falls at Otter Creek – There’s a pretty waterfall right in the center of town, with great views from the pedestrian bridge.
  • Visit the Middlebury College campus – Walk the open green, explore public art, or just enjoy the peaceful setting.
  • Grab a local brew or ice cream – Middlebury has a nice mix of pubs, coffee spots, and dessert stops.
If you like small-town charm but don’t want anything too touristy, Middlebury is an easy win for a quick road trip from Rutland.

2. Vergennes & Lake Champlain Views (Addison County)

Drive time from Rutland: about 1 hour 15 minutes Vergennes calls itself Vermont’s smallest city, but it punches way above its weight. Pair a visit here with some Lake Champlain time for a full day out. Ideas for your Vergennes day trip:
  • Walk downtown Vergennes – Cute shops, historic buildings, and a relaxed atmosphere.
  • Stop at Vergennes Falls Park – A short walk takes you to a powerful waterfall on Otter Creek.
  • Head out toward Lake Champlain – Drive west out of town for rolling farm views and lake access points.
  • Picnic by the water – Pack sandwiches in Rutland and enjoy them with a lake view.
On a clear day, the sunset over Lake Champlain is worth the drive all by itself.

3. Brandon Gap & Moosalamoo Scenic Area (Addison County side)

Drive time from Rutland: about 30–45 minutes If you love quiet drives, mountain views, and trailheads that aren’t crowded, head toward Brandon Gap and the Moosalamoo region on the Addison County side. What to do around Brandon Gap:
  • Scenic drive over Route 73 – Winding, wooded, and full of mountain scenery.
  • Hiking opportunities – There are several trailheads near the Gap; some are short viewpoints, others more serious hikes.
  • Leaf peeping in fall – This is one of those drives where the trees seem to glow.
Even if you don’t hike, just cruising with the windows down and stopping at turnouts to take in the views makes this a refreshing half-day escape from Rutland.

4. Manchester, VT – Shopping, Food & Mountain Views (Bennington County)

Drive time from Rutland: about 1 hour Manchester is one of the top day-trip destinations from Rutland. It blends upscale outlets with local shops, plus great views of the Green Mountains. Highlights in Manchester:
  • Downtown shops and outlets – Clothing, outdoor gear, local crafts—easy to spend an afternoon browsing.
  • Walk around town – Sidewalks, historic inns, and cozy cafés make it very walkable.
  • Scenic back roads – The roads around Manchester offer classic Vermont barns, meadows, and mountain views.
If you’re craving a mix of “small town” and “treat yourself,” Manchester is a smart pick.

5. Bennington, VT – History, Art & a Famous Monument (Bennington County)

Drive time from Rutland: about 1 hour 15 minutes–1 hour 30 minutes Bennington has a strong historic feel, with a little bit of everything: museums, art, and one huge monument you can’t miss. Things to see in Bennington:
  • Bennington Battle Monument (outside grounds) – Even just seeing it from the outside is impressive. It’s one of Vermont’s tallest structures.
  • Old churches and cemeteries – If you like history, the old graveyards and churches tell a lot of local stories.
  • Art galleries and studios – Keep an eye out for local pottery and handmade goods.
  • Walk across one of the nearby covered bridges – The area is known for them, and they’re a classic New England photo op.
If you enjoy combining history with a relaxed town walk, Bennington makes a great full-day road trip from Rutland.

6. Woodstock, VT – Picture-Perfect New England Village (Windsor County)

Drive time from Rutland: about 1 hour Woodstock is one of the most photogenic towns near Rutland. White churches, tidy village greens, and historic homes make it look like a movie set. Top things to do in Woodstock:
  • Stroll the village green – Browse shops, bakeries, and galleries around the main square.
  • Walk to a covered bridge – Woodstock has a couple of very charming bridges within walking distance of downtown.
  • Drive the back roads – The roads just outside town are full of farms, stone walls, and mountain views.
If you want a classic “Vermont village” experience, Woodstock is hard to beat.

7. Quechee Gorge & Quechee Village (Windsor County)

Drive time from Rutland: about 1 hour 15 minutes Quechee is famous for one big thing: the “Little Grand Canyon of Vermont,” also known as Quechee Gorge. What to do in Quechee:
  • View Quechee Gorge from the bridge – The main bridge on Route 4 gives you a dramatic look straight down into the river.
  • Walk along the rim trails – Short, easy trails follow the edge of the gorge on both sides.
  • Explore Quechee Village – Nearby shops, glassblowing studios, and cafes make it easy to fill out the day.
This road trip from Rutland is great if you love simple hikes with big payoffs.

8. Ludlow & Okemo Area (Windsor County)

Drive time from Rutland: about 40–50 minutes Ludlow sits at the base of Okemo Mountain and makes a solid year-round road trip from Rutland—even if you’re not skiing. Ideas for your Ludlow trip:
  • Walk Main Street – Small-town shops, pizza places, and coffee spots give Ludlow an easy-going feel.
  • Scenic drives around Okemo – The roads around the mountain are pretty in all seasons, especially in fall.
  • Nearby lakes – A short drive from town gets you to quiet lakes where you can relax by the water.
If you want something close, simple, and relaxed, Ludlow is one of the easiest Rutland getaways.

9. Granville, NY – Slate Valley & Small-Town New York (Washington County, NY)

Drive time from Rutland: about 35–45 minutes Just across the state line, Granville sits in New York’s Slate Valley. It’s a quiet area with rolling hills and a different feel from Vermont, even though it’s so close. Things to enjoy around Granville:
  • Drive the back roads – The countryside here is wide open, with farms, quarries, and views of the hills.
  • Check out local diners or cafés – It’s fun to compare your “regular” Vermont haunts with small-town New York spots.
  • Explore nearby small villages – Washington County has a handful of tiny towns worth a quick drive-through.
If you’re curious about what’s just over the border from Rutland, Granville is an easy first step.

10. Lake George, NY – Classic Adirondack Getaway (Washington County Area)

Drive time from Rutland: about 1 hour 15 minutes–1 hour 30 minutes If you’re up for a slightly longer drive, Lake George makes a great mini-escape. It has that “old-school summer vacation” vibe, with a mix of nature and classic attractions. Things to do at Lake George:
  • Walk the lakefront – Enjoy mountain views, boats on the water, and plenty of benches to sit and take it all in.
  • Boat tours – Sightseeing cruises are a relaxing way to see more of the lake.
  • Browse the village – Souvenir shops, ice cream, arcades, and family-friendly restaurants line the main streets.
This is a fun choice if you’re traveling with kids or want that “busy summer town” feel, especially after quiet days in Rutland.

Tips for Planning Your Rutland Road Trips

To make your out-of-county adventures smoother, keep a few simple things in mind:
  • Check drive times – Most spots listed are within about 30 minutes to 1.5 hours of Rutland.
  • Watch the seasons – Winter driving in Vermont and upstate New York can be tricky; fall and summer are especially beautiful.
  • Pack snacks and water – Once you leave town, services can get sparse in rural areas.
  • Bring layers – Mountain areas can be breezy, even in late spring and early fall.
When I drive out of Rutland, I like to keep the schedule loose. Some of the best finds happen when you pull over for a random farm stand, a roadside view, or a tiny café you didn’t plan on.

Where Will You Go Next?

From Middlebury’s waterfalls to Woodstock’s village green, from the dramatic Quechee Gorge to the shores of Lake George, there’s a surprising amount to see within a short drive of Rutland, VT—without ever repeating the same day trip twice. Which of these road trips from Rutland would you try first? Are you more into quiet drives and scenery, or do you want busy towns with lots of shops and restaurants? Share your thoughts in the comments—and if you’ve got a favorite out-of-county spot near Rutland that I didn’t mention, I’d love to hear about it. If you found this guide helpful, please share it with friends, family, or anyone in Vermont looking for new day-trip ideas. Your shares and comments help more travelers discover fun things to do near Rutland, Vermont.
Location: Georgetown, IN, USA

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