10 Best Short Road Trips From Proctor, Vermont (Rutland County)

on

10 Easy Road Trips From Proctor, Vermont: Fun Things To Do Just Beyond Rutland County

If you’re based in Proctor, Vermont (in Rutland County) and feel like you’ve already checked out everything close by, don’t worry. There’s a whole world of small towns, mountains, lakes, and historic villages waiting just a short drive away in nearby counties. In this guide, we’ll look at 10 short out-of-county road trips to fun things to do near Proctor, focusing on:
  • Washington County, NY
  • Addison County, VT
  • Bennington County, VT
  • Windsor County, VT
Each spot is an easy day trip, and many can turn into a relaxed weekend getaway. So grab a coffee, fill up the gas tank, and let’s hit the road.

1. Cross the State Line to Charming Manchester, VT (Bennington County)

About an hour south of Proctor, Manchester, Vermont in Bennington County feels like a classic New England postcard come to life. Why go: It’s the perfect mix of small-town charm, shopping, food, and mountain views. Things to do in Manchester:
  • Shop the outlets: You’ll find big names and local boutiques along Main Street and in the outlet area. It’s a great place to refresh your wardrobe before winter or summer.
  • Visit Hildene, The Lincoln Family Home: Tour the stately home of Robert Todd Lincoln, Abraham Lincoln’s son, walk the gardens, and soak in wide mountain views.
  • Explore Manchester Village: Stroll past white churches, historic inns, and picture-perfect streets. It’s especially beautiful in the fall.
  • Outdoor time at Equinox Preserve: Hike the wooded trails on the lower slopes of Mount Equinox for peaceful forest time without a huge climb.
If you like a mix of history, shopping, and gentle outdoor time, Manchester makes an easy full-day road trip from Proctor.

2. Step Back in Time in Bennington, VT (Bennington County)

Continue a bit farther south (about 1.5 hours from Proctor) and you’ll hit Bennington, Vermont, also in Bennington County. It has deep Revolutionary War history and a classic small-town feel. Highlights in Bennington:
  • Bennington Battle Monument: Ride the elevator to the top of this impressive stone monument for wide views of Vermont, Massachusetts, and New York. On a clear day, you can see for miles.
  • Old First Church and Cemetery: Walk around one of Vermont’s most beautiful churches and visit the grave of poet Robert Frost.
  • Bennington Museum: Check out local art, Vermont history, and exhibits about the Battle of Bennington and regional culture.
  • Covered bridges drive: There are several photogenic covered bridges nearby. Create your own little “bridge loop” and stop for photos.
If you love American history and pretty drives, Bennington is a great road trip from Proctor.

3. Discover Art, Coffee, and Culture in Brattleboro, VT (Windsor Adjacent)

While Brattleboro is in Windham County, many people from Proctor pair a trip through Windsor County with a stop here, since it’s roughly 2 hours southeast and easy to reach along the Connecticut River corridor. Why it’s worth the drive: Brattleboro has a laid-back, artsy vibe that’s different from many Vermont towns. What to do:
  • Walk downtown: Browse independent bookstores, record shops, and galleries. Grab a latte and people-watch from a sidewalk table.
  • Enjoy the riverfront: Walk along the Connecticut River and take in the bridge views, especially pretty at sunset.
  • Local food scene: You’ll find plenty of vegetarian-friendly spots, bakeries, and farm-to-table restaurants.
If you’re craving a different kind of Vermont, a full-day road trip through Windsor County down to Brattleboro is a fun change of pace.

4. Farm Charm & Lake Views in Vergennes, VT (Addison County)

Head about an hour northwest from Proctor into Addison County, and you’ll find Vergennes, Vermont’s smallest city. It may be small, but it has a surprising amount to do. Top things to do in Vergennes:
  • Walk downtown: Main Street is lined with brick buildings, local shops, and cozy restaurants. It’s very walkable.
  • Check out Vergennes Falls Park: Just off downtown, the falls on Otter Creek make for a beautiful photo spot and a nice place to sit and relax.
  • Day trip to Lake Champlain: Just a short drive away, you can access several lakefront spots with boat launches, picnic areas, and views of the Adirondacks.
Vergennes is a great “slow day” trip from Proctor—no rush, just wandering, eating, and enjoying the water and mountain views.

5. Explore Historic Middlebury, VT (Addison County)

About 45–60 minutes from Proctor, Middlebury in Addison County is a college town with a historic downtown and river views. Why visit Middlebury:
  • Scenic downtown: Stroll across the pedestrian bridge over Otter Creek and admire the falls. The old stone buildings make you feel like you’ve stepped into another era.
  • Local shops and cafes: Grab a sandwich, ice cream, or a craft beer, and take your time exploring independent bookstores and boutiques.
  • Middlebury College campus: Walk around the campus green and art museum (check open hours). It’s peaceful and beautifully maintained.
If you enjoy a mix of river scenery, history, and a relaxed college-town vibe, Middlebury is one of the easiest and most rewarding short drives from Proctor.

6. Classic Vermont Lake Life at Lake Dunmore & Branbury State Park (Addison County)

In Addison County, just north of Middlebury, you’ll find Lake Dunmore and Branbury State Park, roughly an hour from Proctor depending on your route. What makes it special: It’s the classic Vermont “lake day” experience without having to drive all the way to the ocean. Things to do:
  • Swim and relax on the beach: The park has a nice sandy area that’s great for families and anyone who just wants to float and chill.
  • Picnics with a view: Pack a cooler, spread out a blanket, and enjoy lunch with the Green Mountains rising behind the lake.
  • Kayaking or canoeing: If you have your own kayak or canoe, this is a beautiful, manageable-size lake to paddle.
On hot summer days, this is one of the best road trips from Proctor if you’re craving water and a break from your usual routine.

7. Mountain Views & Maple in Woodstock, VT (Windsor County)

About 1.5 hours east of Proctor sits the picture-perfect village of Woodstock in Windsor County. Many people say it’s one of the prettiest towns in Vermont—and it’s not hard to see why. What to do in Woodstock:
  • Stroll the village green: Walk past historic homes, browse galleries and shops, and enjoy the peaceful small-town vibe.
  • Visit Billings Farm & Museum: Learn about Vermont’s farming history, meet the animals, and get a feel for traditional farm life.
  • Drive to Quechee Gorge (nearby in Windsor County): Stop at the “Little Grand Canyon of Vermont,” peek over the bridge, and hike down if you’ve got the energy.
Woodstock is perfect if you want that “classic Vermont” look—white fences, big trees, and cozy inns—without driving all day.

8. Quechee Gorge & Glassblowing in Quechee, VT (Windsor County)

Just a short drive from Woodstock, Quechee in Windsor County makes a great add-on or its own day trip from Proctor. Why go: It’s all about big views and unique local crafts. Don’t miss:
  • Quechee Gorge: Stand on the bridge and look down at the river, about 165 feet below. The view is especially stunning in fall.
  • Quechee State Park: Hike the rim trails or head down near the water for a different perspective of the gorge.
  • Simon Pearce glassblowing: Watch artisans blow glass in a riverside mill building. Then visit the shop and, if you like, stay for a meal overlooking the waterfall.
If you enjoy scenic views and watching craftspeople at work, Quechee is a must-do road trip from Proctor.

9. Cross Into New York: Scenic Lake George, NY (Washington & Warren Adjacent)

While Lake George is mainly in Warren County, New York, it’s commonly visited from Washington County and is a classic summer road trip from southern Vermont. From Proctor, you’re looking at about 1.5–2 hours, depending on your route. Why you’ll love Lake George:
  • Boat cruises: Take a scenic cruise on the lake for mountains-on-all-sides views. It’s a simple way to relax and see the area.
  • Swim and sunbathe: Public beaches and swimming areas around the lake make this a great warm-weather getaway.
  • Mini-golf, arcades, and family fun: The main village area is full of kid-friendly (and kid-at-heart-friendly) attractions.
If Proctor feels a little too quiet in midsummer, Lake George gives you that buzzing “vacation town” feel without requiring a long, exhausting drive.

10. Small-Town New York Vibes in Fort Edward & Hudson Falls (Washington County, NY)

Just over the border into Washington County, New York, towns like Fort Edward and Hudson Falls offer a different kind of small-town experience about 1.5 hours from Proctor. What to check out:
  • Hudson River views: Walk along the river, enjoy the parks, and watch the water flow past old industrial sites and historic buildings.
  • Local diners and bakeries: Grab breakfast or lunch at a no-frills, hometown spot. Sometimes the best part of a road trip is the pie and coffee.
  • Historic stops: This region played a role in early American history, and you’ll often stumble across monuments, markers, and small museums.
If you’re curious what’s just beyond the Vermont border, Washington County makes an easy “change of scenery” trip from Proctor.

Tips for Making the Most of Your Road Trips From Proctor

  • Plan around the seasons:
    • Summer: Lakes like Dunmore and Lake George are perfect.
    • Fall: Woodstock, Quechee, and Manchester shine with foliage.
    • Winter: Manchester and Woodstock feel extra cozy with snow.
    • Spring: Brattleboro and Middlebury are great for riverside walks and early hikes.
  • Travel time sweet spot: Most of these places are 45 minutes to 2 hours away—ideal for a day trip that doesn’t require leaving at sunrise.
  • Pack smart: A small cooler, water bottles, a light jacket, and comfortable walking shoes go a long way in New England, where weather can change fast.

What’s Your Favorite Road Trip From Proctor?

Living in or visiting Proctor, Vermont, doesn’t mean you’re limited to just one county. With Bennington, Windsor, Addison, and Washington counties all within reach, you can easily turn a regular weekend into a mini vacation. Have you driven to any of these spots from Proctor? Did I miss a favorite small-town cafĂ©, hike, or hidden lookout? Share your go-to road trips in the comments so other travelers can discover them too. And if you found this guide helpful, please share it with friends or family who are planning a Vermont getaway—it might inspire their next day trip from Proctor.
Location: Georgetown, IN, USA

Comments

Post a Comment