The Ultimate Vermont Road Trip Itinerary

By Carly Eisley

They don’t call Vermont the Green Mountain State for nothing! This New England gem is home to mountains, lakes, swimming holes, waterfalls, miles (and miles, and miles, and miles) of trails, lush green landscapes, and some of the best craft beer in the country. The border is only 4 hours from our New York Escape rental location. What’s not to love?

When should you visit? Hit the road in the Summer for lush green landscapes, cascading waterfalls, hiking galore, and lake swimming. The foliage in the Fall is to DIE FOR. Winter means snow sports are in full swing with a multitude of areas for downhill and cross-country skiing, snowboarding, snowshoeing, and ice fishing. Spring…. well, Spring means mud season and black flies. From mid-March to early May (usually), many outdoor areas are messy at best or even closed to protect the trails so plan accordingly (aka don’t plan an early spring Vermont road trip).

So, without further ado, here are a few favorite stops for a stellar Vermont road trip in your campervan or car! I highly recommend avoiding the highways whenever possible, check your map/atlas and get spontaneous. Vermont’s back roads are FULL of hidden treasures to explore!

Brattleboro

Approaching Vermont on route 91 from the south, Brattleboro is one of the first stops you’ll want to make. Hit their food co-op for some organic snacks and groceries, and then stroll downtown to unique storefronts and coffee shops. Take in the quintessential covered bridge, visit art museums and galleries, and stretch your legs on some of the nearby trails.

From here, head north toward Mount Ascutney and Woodstock. Take a side trip to the Vermont Country Store for some local wares in a general store-like atmosphere. Don’t miss the local cheese and some penny candy!

Another nice side trip is to the little village of Grafton. Take a hike (or snowshoe!) at the Grafton outdoor center and nosh on some local foods at the Grafton village store (MKT) before hitting the road.

Woodstock

Woodstock and its surrounding areas offer a host of beautiful and unique places to explore. The small downtown of Woodstock has shops and restaurants for a little taste of civilization. Head to Billings Farm while you are there, to tour a Vermont rural heritage museum and working farm. The Ottaquechee river runs along route 4. Find yourself a place to stop soak your feet or take a dip!

To the east, nearby Quechee gorge is home of the “little Grand Canyon” of Vermont: a large chasm in the earth with the river running below. Camp at Quechee state park and check out the Simon Pearce glassblowing demonstration in town.

A bit south of Woodstock is the Ascutney/Brownsville area. Camping is available at Mount Ascutney state park, and from there you can hike to the fire tower at the top of Mount Ascutney. Mountain bike or hike the Sport Trails of Ascutney Basin (STAB) trails, and refuel after a day of exploring at the Brownsville Butcher and Pantry, a local farm to table restaurant and market.  Looking for a destination mountain bike or trail running race? This area is home to the legendary Vermont 100-mile trail running ultramarathon held every July, and the Vermont 50-mile mountain bike and 50 mile/50-kilometer trail run in September.

*There are a few camping options in this area, including Mount Ascutney state park, Wilgus State Park, or Quechee state park*

Groton

Looking for a little solitude? Head north from Woodstock to Groton, VT. Home to the Groton State Forest as well as seven state parks offering camping, lakes, and hiking/biking trails, this is a nature lover’s dream!

Northeast Kingdom

Head (you guessed it) northeast to Burke, Vermont, home of a vast network of mountain biking trails known as Kingdom Trails. This area is a premier destination for mountain bikers in the northeast, with fat biking, xc skiing, and snowshoeing available on the trails in the winter as well. Bike rentals are available from local shops such as East Burke Sports and the Village Sport shop, so don’t worry if you left your ride at home and are itching to hit the dirt.  After a day of riding, enjoy a local craft brew with a view at the SpokeEasy lounge at the Wildflower Inn. Stop by Auntie Dee’s baked goods on Burke Mountain Road for some home-baked delights before you head out of town. The croissants are to die for!

Camp at the breathtaking campsite on the property of Wooly Buggah Barn, minutes from the trails and the shores of Lake Willoughby. Additional list of some developed camping areas is available here.

Once you’ve had your fill of fat tires, head over to route 100 and start making your way south. A great stopover en route from the Northeast Kingdom to the Stowe area is Elmore State Park. Camp along the lake and take a hike to the fire tower at the top of Mount Elmore for some amazing scenery!

Stowe & Waterbury

This mountain town is home to some excellent skiing, hiking, a very New England-y downtown, and renowned brewery The Alchemist (of Heady Topper fame). Work up an appetite with some hiking (nearby Mt. Mansfield is Vermont’s highest peak at 4,395 feet).  Another great Vermont hiking destination is Camel’s Hump, to the southwest of Waterbury.

In the warmer months, I highly recommend renting paddleboards or kayaks and exploring the Waterbury reservoir. The view of the mountains from the water is outstanding! Stop by the iconic Ben & Jerry’s ice cream factory for a tour and a cone. In the mood for some dinner cooked indoors, by someone else? Prohibition Pig has some very tasty BBQ and a brewery as well. Don’t skip the Cold Hollow Cider Mill for fresh apple cider and cider donuts, perfect in any season!

Looking to hit the slopes in winter?  Stowe Mountain, Smuggler’s Notch, and Bolton Valley ski areas are all nearby.

Little River State Park in Waterbury has some amazing camping along the Waterbury Reservoir and is a nice central location to explore this area. Underhill State Park is the trailhead for Mount Mansfield and has some walk-in tent sites.

Burlington

Take a side trip to the west and explore the quirky downtown of Burlington, Vermont’s “big city.” Shop, eat, and people watch at the Church Street Marketplace, an open-air mall that hosts, among other things, a jazz festival and art festival days. Take in some of the city’s art murals. Check off some boxes on your Vermont brewery trail passport; brew tours are available, and several breweries are in walking distance. Enjoy the bike path along Lake Champlain and hop on a boat or ferry to explore some of the smaller islands along the coast.

Change your mind and decide you want to head out of Vermont instead? Take the car ferry from Burlington over to New York for some Adirondacks exploring.

Mount Philo State Park to the south of Burlington has a small (7 site) campground. There are also numerous camping areas and parks north of Burlington along Lake Champlain.

Route 100 South

Ok… I know this is not a town. Enter the “choose your own adventure” portion of this road trip. From Waterbury, head south on Vermont’s route 100 for a scenic drive worthy of many, many stops. There are swimming holes, waterfalls, historic sites, hiking trails, and quaint little towns just waiting for you to pop in. This drive follows along the eastern border of the Green Mountain National Forest, and the outdoor opportunities and scenery are outstanding. If you need a few ideas to get you going, you can check out…

Swimming Holes

• Lareau swimming hole in Waitsfield: this can get busy on summer weekends but is worth a stop if you are looking for a place to take a dip!
• Warren Falls in Warren: another nice stop for a waterfall and swimming hole
• Buttermilk Falls in Ludlow

These are just some ideas. Almost all of Vermont’s main back roads follow some body of water, with many, many opportunities to soak in the stream and river waters (as long as the currents aren’t too high! Always be safe and use common sense.)

Killington

The Killington area is a great stopover on Route 100. Camp at Gifford Woods State Park or Coolidge State Park for some very nice sites with great views of the nearby mountains. Take a hike on the Appalachian Trail or Vermont’s Long Trail. In Winter months, ski Killington and Pico mountains. Visit McGrath’s Irish Pub for some expert Guinness foam art, or head over to the Long Trail brewery for a cold brew in an Adirondack chair overlooking the river below.

Bennington

Visit the Robert Frost Stone House Museum, and the gravesite of the late poet in this small southern Vermont town. Hop on the Appalachian Trail for an out and back hike overlooking the area. Camp at Woodford State Park, set on a mountain plateau (at 2400 feet) bordered by the Green Mountain National Forest with a lake and hiking trails.

Camping Resources

• Vermont State Parks website, with an interactive map searchable by parks that offer camping
• Vermont Campground Association website, with a map of both state and private campgrounds
• Green Mountain National Forest camping areas (some free dispersed camping is available, but not much!)
• Hipcamp for some unique private camping areas
• The Dyrt is a campground website with reviews, search “Vermont” for top-rated campgrounds. Leave your own reviews to be entered into prize drawings every month! You can also save campgrounds into a list, making pre-trip planning a breeze.
• FreeCampsites.net is a good resource for free camping, be mindful of the area you are headed as listings may not be 100% accurate or up to date.

And there you have it! A starter itinerary for your Vermont adventure. There are SO many more places to explore, whether you’re in a car or renting a campervan, so get out there and find some favorites of your own.