10 Easy Road Trips Near Hartford Village, Vermont (That Take You Out of Windsor County)
If you’re based in
Hartford Village, VT and itching to explore beyond Windsor County, you’re in a perfect spot. Within about one to two hours, you can reach small towns, mountain trails, breweries, covered bridges, and classic New England main streets in neighboring counties of Vermont and New Hampshire.
This guide shares
10 short out-of-county road trips from Hartford Village into nearby counties like Grafton and Sullivan in New Hampshire, plus Addison, Bennington, Orange, Rutland, and Windham in Vermont.
Think of it as your “weekend playbook” for
things to do near Hartford Village—without repeating the same local spots over and over.
1. Hanover & Lebanon, NH (Grafton County) – College Towns with Coffee, Culture, and Trails
Driving time from Hartford Village:
about 15–20 minutes (depending on traffic)
If you want something close but still “out of county,” head across the river into
Grafton County, New Hampshire. Hanover and Lebanon feel like Hartford’s smart and artsy cousins.
What to do:
- Stroll around Dartmouth College (Hanover): Walk the green, peek into the Baker-Berry Library, and wander through the campus like you’re back in college for a day.
- Dartmouth Green & Main Street: Grab coffee, sit on a bench, and people-watch. It’s simple, but it’s one of the best free things to do near Hartford Village.
- Hood Museum of Art: A surprisingly rich collection, usually with free admission. It’s an easy indoor option on a rainy day.
- Lebanon’s Colburn Park: A classic New England town green with shops and places to eat within a short walk.
Local tip: If you go in fall, leave a little early and take your time. The drive from Hartford Village to Hanover during foliage season is like scrolling through a live postcard.
2. Claremont & Sunapee Region, NH (Sullivan County) – Mills, Mountains, and Lake Time
Driving time from Hartford Village:
about 30–45 minutes
A short ride south on I‑91 and across the river lands you in
Sullivan County, New Hampshire. It’s a mix of old mill town history and laid-back lakes and mountains.
What to do:
- Explore Downtown Claremont: Brick mill buildings, a river, and a small but growing food scene.
- Walk along the Sugar River: There are easy paths near the old mills, great for stretching your legs mid-drive.
- Head toward Lake Sunapee: If you don’t mind a slightly longer drive, the Sunapee area has swimming, boating, and hiking.
- Mount Sunapee (in season): Skiing in winter, hiking in summer. It’s a solid day trip from Hartford Village if you’re craving some elevation.
Why go: When you’re tired of your usual weekend loop, Claremont and Sunapee offer that “small adventure” feeling without needing to book a hotel.
3. Middlebury, VT (Addison County) – College Charm and Covered Bridges
Driving time from Hartford Village:
about 1 hour 15 minutes–1 hour 30 minutes
If you’re looking for a
classic Vermont day trip, Middlebury in
Addison County checks almost every box: a pretty college campus, a river running through town, nearby farms, and breweries.
What to do:
- Wander Middlebury College: The campus has open lawns, mountain views, and public art.
- Check out the falls downtown: The river drops right through the village, making for great photos and a nice soundscape while you walk.
- Visit nearby covered bridges: The area around Middlebury has some very photogenic bridges—perfect for a slow Sunday drive.
- Grab local eats: From coffee shops to sit-down spots, there’s no shortage of tasty stops.
Road trip tip: Take Route 125 or other back roads when you can. The hills, barns, and open fields feel like driving through a Vermont travel magazine.
4. Vergennes & Lake Champlain Views, VT (Addison County)
Driving time from Hartford Village:
about 1 hour 30 minutes–1 hour 45 minutes
Vergennes calls itself
Vermont’s smallest city, but what it lacks in size, it makes up for in charm—and proximity to
Lake Champlain.
What to do:
- Stroll Vergennes’ Main Street: A short but sweet downtown with shops and restaurants.
- Head toward Basin Harbor or nearby lake access points: Perfect for a picnic and sunset views over Lake Champlain.
- Stop at farm stands in season: Grab fresh corn, berries, or maple products along the way.
Why it’s worth the drive: From Hartford Village, this trip gives you a totally different vibe—water views instead of just mountains, but still very “Vermont.”
5. Bennington, VT (Bennington County) – Monuments, Museums, and Mountain Views
Driving time from Hartford Village:
about 2 hours
If you’re up for a slightly longer day trip, head south and west to
Bennington County. Bennington is rich in history and feels quietly grand, with mountain ridges all around.
What to do:
- See the Bennington Battle Monument: A towering stone monument you can spot from miles away. Go up for broad views of the surrounding mountains and town.
- Explore Old Bennington: Quiet streets, historic homes, and a beautiful hilltop cemetery with famous names.
- Visit local galleries and shops: The town has a nice mix of art, antiques, and Vermont-made goods.
Drive tip: Consider making this a full-day loop with a stop in Rutland or a small town along the way. It breaks up the drive and turns one road trip into two mini adventures.
6. Manchester, VT (Bennington County) – Shopping, Scenic Drives, and Mountain Luxury
Driving time from Hartford Village:
about 1 hour 45 minutes–2 hours
Manchester is one of those Vermont towns that feels both upscale and relaxed. It’s a favorite for
weekend getaways from around New England, and it’s still doable as a day trip from Hartford Village.
What to do:
- Browse the outlets and local shops: From outdoor gear to clothing and local goods.
- Drive around the back roads: You’ll find sweeping mountain views, stone walls, and classic Vermont scenery.
- Stop at nearby trails or scenic lookouts: The Green Mountains around Manchester are full of short hikes and overlooks.
Why go: When you want a road trip from Hartford Village that includes both shopping and scenery, Manchester hits the sweet spot.
7. Randolph, VT (Orange County) – Small-Town Vermont with an Artsy Side
Driving time from Hartford Village:
about 40–50 minutes
Head north into
Orange County and you’ll find Randolph, a low-key town with just enough going on to fill an easy afternoon.
What to do:
- Walk downtown: Pop into local shops, grab coffee, and check out any community events that might be happening.
- Drive the back roads: Randolph is surrounded by rolling hills and farms that look especially good in early morning or late afternoon light.
- Catch a show or live music (in season): The town has an artsy streak, so check local listings before you go.
Perfect for: Those lazy Sundays when you want to get out of Hartford Village, but don’t want to spend half the day in the car.
8. Barre & Montpelier Edges (Orange County Side), VT – Granite and State-Capital Energy
Driving time from Hartford Village:
about 1 hour
While Montpelier itself stretches into Washington County, the greater area nudges up against
Orange County. Pair that with nearby
Barre, and you get a mix of old-school industry and small-city feel.
What to do:
- Visit Barre’s granite heritage sites: The region is famous for its stonework and monuments.
- Walk the downtown areas: Both Barre and the Montpelier area have interesting streets to explore, plus cafés and bakeries.
- Snap photos of historic buildings and churches: The architecture alone can fill a photo roll.
Road tip: On the way back to Hartford Village, consider taking quieter back roads instead of just the interstate. You may add a few extra minutes, but gain a lot of scenery.
9. Rutland & Nearby Trails, VT (Rutland County) – City Conveniences, Mountain Backdrop
Driving time from Hartford Village:
about 1 hour 15 minutes–1 hour 30 minutes
If you want more options—bigger grocery stores, more restaurants, and access to the mountains—
Rutland County is a solid pick.
What to do:
- Explore downtown Rutland: Murals, shops, and restaurants give you a little of that “small city” buzz.
- Use Rutland as a base: From here you’re close to hiking, biking, and skiing areas (including the broader Killington region).
- Check local events: Markets, festivals, and outdoor concerts pop up throughout the year.
Why it’s handy: When you need a day trip from Hartford Village that mixes errands with fun, Rutland lets you do both in one go.
10. Brattleboro, VT (Windham County) – Artsy, Bohemian, and Right on the River
Driving time from Hartford Village:
about 1 hour 15 minutes–1 hour 30 minutes
For a different flavor of Vermont, head south to
Windham County and spend a day in Brattleboro. It feels creative, slightly bohemian, and very alive.
What to do:
- Walk downtown Brattleboro: Independent bookstores, art shops, cafés, and a lively main street.
- Enjoy the Connecticut River views: The town sits right along the water, and some overlooks are especially pretty at sunset.
- Sample local food and drink: From bakeries to breweries, you can easily turn this into a “taste of Brattleboro” tour.
Best for: When you want a road trip that feels like an actual “mini vacation” from Hartford Village, not just a quick errand run.
Making the Most of Your Hartford Village Road Trips
Living in or near
Hartford Village, Vermont puts you within easy reach of
New Hampshire’s river towns, Vermont’s lake country, historic villages, and mountain hubs. With these 10 out-of-county ideas, you can:
- Plan easy day trips from Hartford Village
- Discover new things to do near Hartford Village, VT
- Mix quick drives with longer weekend adventures
You don’t need a full week off or a plane ticket. Sometimes, a one- or two-hour drive in any direction is enough to reset your mind, see something new, and remember why people love this corner of New England.
Share Your Favorite Spots Near Hartford Village
Have you taken any of these road trips from Hartford Village? Did I miss a must-see stop in Grafton, Sullivan, Addison, Bennington, Orange, Rutland, or Windham County?
- Drop a comment with your favorite drives, hikes, cafés, or photo spots.
- Share this post with friends, family, or coworkers who live in the Upper Valley and are always saying, “We should get out more this weekend.”
The more we share our local tips, the easier it becomes for everyone to discover fresh, fun
things to do near Hartford Village, Vermont—without ever needing to go very far from home.
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