10 Best Short Road Trips from White River Junction, Vermont

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10 Easy Road Trips From White River Junction, Vermont (All Outside Windsor County)

Planning a visit to White River Junction, Vermont and looking for fun day trips nearby? Or maybe you live in the Upper Valley and just need a change of scenery without spending hours in the car. You’re in luck. White River Junction sits at a crossroads, which makes it a perfect base for short road trips in Vermont and New Hampshire. In about 30–90 minutes you can reach waterfalls, classic small towns, mountain views, breweries, covered bridges, and even a famous alpine slide. Below are 10 easy out-of-county road trips from White River Junction, all in neighboring counties:
  • Grafton County, NH
  • Sullivan County, NH
  • Addison County, VT
  • Bennington County, VT
  • Orange County, VT
  • Rutland County, VT
  • Windham County, VT
Each trip includes an approximate drive time from White River Junction, so you can pick the one that fits your day.

1. Hanover & Lebanon, NH – Ivy League Charm and Riverfront Trails (Grafton County)

Drive time: About 10–20 minutes County: Grafton County, New Hampshire Just across the Connecticut River, the twin towns of Hanover and Lebanon make one of the easiest road trips from White River Junction. What to do in Hanover:
  • Stroll through the Dartmouth College campus – brick buildings, wide greens, and that classic Ivy League feel.
  • Walk or bike along the Connecticut River on local paths and park areas.
  • Browse indie bookstores and small shops in downtown Hanover.
What to do in Lebanon:
  • Relax on the Lebanon Town Green, often hosting concerts and markets in warmer months.
  • Walk the Rail Trail that runs through town for an easy, flat stroll.
  • Enjoy coffee shops and local restaurants clustered around the green.
It’s an easy half-day trip: grab a coffee in Hanover, wander the campus, then head to Lebanon for an early dinner.

2. New London & Lake Sunapee, NH – Lakeside Escape (Sullivan County)

Drive time: About 45–55 minutes County: Sullivan County, New Hampshire If you’re craving water views and small-town charm, head east toward Lake Sunapee and the town of New London. Ideas for your visit:
  • Walk through New London’s main street with its shops, cafés, and the feel of a classic New England college town.
  • Visit Lake Sunapee for swimming in summer, leaf-peeping in fall, or just peaceful lakeside views any time of year.
  • Stop at roadside farm stands along the way for fresh produce and baked goods.
On a sunny day, this drive feels like a mini-vacation. Pack a picnic, some folding chairs, and take your time along the lake.

3. Quechee Gorge’s “Back Door”: Taftsville & Woodstock Area Backroads (Orange County)

Drive time: About 25–40 minutes (via backroads avoiding Windsor County stops) County: Orange County, Vermont (approaching the Woodstock/Quechee region from the north and east) You’ll technically route around Windsor County points of interest, but you can still enjoy the scenery from the Orange County side. What makes this trip fun:
  • Drive scenic backroads through Orange County, passing rolling hills, old barns, and maple stands.
  • Pause at small-town general stores for coffee and a cookie—this is where you’ll meet real Vermont.
  • Use overlooks and pull-offs to enjoy views toward the Quechee and Woodstock region without actually planning activities inside Windsor County.
This one is more of a slow, scenic drive than a “checklist” outing. It’s perfect when you just want to relax, listen to music or a podcast, and see some classic Vermont landscapes.

4. Middlebury, VT – College Town & Covered Bridges (Addison County)

Drive time: About 1 hour 15 minutes–1 hour 30 minutes County: Addison County, Vermont Middlebury is a lovely small town that feels just the right size—not too busy, not too sleepy. Things to do in Middlebury:
  • Explore Middlebury College campus with its stone buildings and open lawns.
  • Walk downtown to see the falls on Otter Creek right in the center of town.
  • Visit nearby covered bridges for that postcard New England photo.
  • Check out local breweries or cider spots depending on the season.
If you’re coming from White River Junction, the drive itself is part of the fun. You’ll weave through small villages, past farms and views of the Green Mountains.

5. Bristol & the Champlain Valley Backroads (Addison County)

Drive time: About 1 hour 30 minutes County: Addison County, Vermont Bristol sits at the edge of the Green Mountains, with a cute downtown and quick access to some stunning views. How to spend your day:
  • Walk around Bristol’s village green and browse the shops.
  • Drive local roads toward the Champlain Valley for long, wide-open views of fields and distant peaks.
  • Stop at roadside pull-offs for photos and short walks.
If you like a mix of small-town browsing and scenic driving, this route from White River Junction to Bristol and beyond is a good fit. It feels like you’re truly getting away without being too far from home base.

6. Manchester, VT – Outlets, Art, and Mountain Views (Bennington County)

Drive time: About 1 hour 45 minutes–2 hours County: Bennington County, Vermont Manchester is a classic Southern Vermont getaway that draws visitors year-round. It’s a bit longer of a day trip, but still very doable. What you can do in Manchester:
  • Shop at outlets and local boutiques in the walkable downtown area.
  • Visit historic sites and enjoy the carefully kept village streets.
  • Drive the backroads around town for great mountain scenery and foliage in fall.
This is a great spot if you’re traveling with a mix of shoppers and outdoor lovers. One person can browse the stores while another enjoys the views and quiet side streets.

7. Bennington, VT – History and Classic New England Streets (Bennington County)

Drive time: About 2 hours County: Bennington County, Vermont If you’re up for a full-day excursion, head all the way to Bennington, a town rich in early American history. What to look forward to:
  • Wander through historic neighborhoods with stately old homes.
  • Explore downtown shops, galleries, and cafés.
  • Drive the surrounding hills for sweeping views of the Green Mountains.
The road trip from White River Junction to Bennington gives you a chance to see how Vermont changes as you move south—different valleys, different rhythms, but the same laid-back feel.

8. Rutland & Pico Area – Gateway to the Green Mountains (Rutland County)

Drive time: About 1 hour 15 minutes–1 hour 30 minutes County: Rutland County, Vermont Rutland is more of a small city than a town, and it makes a handy base for exploring the western side of the Green Mountains. Ideas for a day trip:
  • Walk around downtown Rutland, which has murals, shops, and restaurants.
  • Use Rutland as a jumping-off point to nearby mountain roads and scenic overlooks.
  • In winter, it’s an easy gateway to ski areas in the region; in summer, you’ll find hiking and swimming spots within a short drive.
If you’re staying in or near White River Junction and want to see a different side of Vermont life, Rutland gives you a more urban feel while still being surrounded by nature.

9. Brattleboro, VT – Artsy Riverside Town (Windham County)

Drive time: About 1 hour 30 minutes–1 hour 45 minutes County: Windham County, Vermont Follow the Connecticut River south and you’ll reach Brattleboro, a lively town with a creative, slightly bohemian vibe. What to enjoy in Brattleboro:
  • Stroll Main Street lined with independent bookstores, galleries, and cafés.
  • Walk down toward the Connecticut River for a peaceful break by the water.
  • Check the local events calendar—there’s often live music, markets, or small festivals.
Brattleboro makes a great road trip if you love local food, art, and people-watching. You can easily spend a whole afternoon just exploring one block at a time.

10. Wilmington & the Southern Green Mountain Byways (Windham County)

Drive time: About 2 hours County: Windham County, Vermont For a true “on the road” experience, aim for Wilmington and the surrounding byways of southern Vermont. How to make the most of it:
  • Stop in Wilmington’s compact village for lunch and a walk.
  • Drive nearby scenic routes through the Southern Green Mountains, especially beautiful in fall.
  • Look for lakes and overlooks along the way to stretch your legs and snap some photos.
This trip feels like a classic New England drive: winding roads, forested hills, and the sense that you’re a bit off the beaten path, even though you’re not far from home.

Tips for Road Trips From White River Junction

A few simple tips can turn a basic drive into a great day out:
  • Keep it flexible: Leave room in your schedule for surprise stops—farm stands, small parks, or a café that looks inviting.
  • Check the season: Some attractions are seasonal, especially in ski towns or lake areas. A quick online check before you go helps.
  • Pack a small bag: Water, snacks, a warm layer (it’s New England, after all), and maybe a blanket for an impromptu picnic.
  • Use the backroads when you can: Highways are faster, but the real Vermont and New Hampshire live on the smaller two-lane roads.

Ready to Explore Beyond White River Junction?

White River Junction is a wonderful base, but some of the best things to do near White River Junction lie just outside Windsor County—in Grafton, Sullivan, Addison, Bennington, Orange, Rutland, and Windham counties. From college towns like Hanover and Middlebury to artsy Brattleboro and historic Bennington, you can pick a different direction each day and still be back in time for dinner. Now it’s your turn:
  • Have you taken any of these road trips from White River Junction?
  • Do you have a favorite small town or scenic drive in Vermont or New Hampshire that I missed?
Share your experiences and tips in the comments—your ideas can help other travelers plan their own adventures. And if you found this guide helpful, please share it with friends or family who are planning a trip to Vermont or the Upper Valley.
Location: Georgetown, IN, USA

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