DISCOVER

We gave you the snapshot, but for those who would like an itinerary with not to miss eateries and destinations - here is a perfectly charming fall road trip in Vermont!

countryside fall woodstock vermont — photo cred: @Jacobxrossi Instagram

Burlington seems to be a great starting point, if you are flying in to Vermont. If you happen to be driving from the south, just pick up in Grafton or Manchester and follow the loop from there.

You set out from Burlington, windows down, first sip of maple latte warming your morning - feeling the weight of your worries fly off the back of the car. On our last trip we landed a Mustang convertible – I can say from first-hand experience that if you have your hair tied back and the heat on, it is an epic experience! Coming from the “big city” of Burlington, as you leave and head SE on Highway 89 before turning north at the darling town of Waterbury, Stowe emerges like a painting—steepled church, crisp mountain air, and bursts of color everywhere

1: Stowe

Stowe welcomes you with the scent of pine only a mountain town can give, storefronts along Main Street, and a skyline dominated by Mt. Mansfield. It’s a place where even the air feels crisp and effervescent. Are you ready to stretch your legs? Hop out and start your wander on the Stowe Recreation Path—a five-mile ribbon winding past wildflower meadows and the iconic red barn at the Vermont Ski and Snowboard Museum. On Sundays, the Stowe Farmers’ Market dishes up cider donuts and local honey. In 2025 the last market is October 19th.

For vistas, take the gondola skyride at Stowe Mountain Resort or drive the dizzying Mt. Mansfield Toll Road (it can cost you a pretty penny, but it is worth it! Try to catch it in the early morning hours or “golden hour” for the best experience) up to panoramic autumn glory.

You can see how you can spend an entire day (or longer) here in this town. Make sure you leave time for some crisp craft beer and hearty mountain fare. For each town we have included a few, but explore and be curious - it is what makes the journey your own!

Dining:

Plate: Said to be one of ten restaurants worthy of a drive from Boston according to Zagat, this restaurant is perfect for a special occasion or a foodie indulgence for the evening.
Doc Ponds: Craft beer meets comfort food. This is what you would expect in a winter ski town, casual and welcoming.
The Bench: Homey, delicious, crowd-pleasing - comfort food. Take out available.
Nearby in the village of Waterbury-
Hen of the Wood: Recently moved to 14 S. Main Street, this restaurant is known as a true “farm-to-table” destination. Open Thursday, Friday, & Saturday for the evening meal.

Boutiques & Shops:

Stowe Mercantile: Retro treats, maple syrup, Vermont whimsy.
Coco Goose Boutique: High-end, boutique featuring designer apparel for women. If you miss them in Stowe, they have a shop in Manchester Center.
Shaw’s General Store: Founded in 1895, shop features casual clothes, footwear and accessories - and always maple syrup.

Top Hikes:

Stowe Pinnacle Trail: 360° views; classic foliage splendor.
Elephant’s Head Cliff: For those seeking sweep and solitude.

Where to Stay:

Stowe Mountain Lodge: Luxe, scenic, and poolside mountain views.
Field Guide Lodge: Funky, boutique, and breakfast magic.
Trapp Family Lodge: Austrian roots, rolling meadows, and sunset bliss.

2: Peacham

Driving east, the world softens—roadside pumpkins, sleepy valleys, and small-town charm greets you in Peacham. Cue the church steeple, tiny library, and that postcard-perfect view of layered hills fading into blue. It’s one of Vermont’s most photographed towns for a reason. This is one of my favorite fall pictures below.

Things to do:

Osmore Pond: Canoe, picnic, or leaf peep by water.
Annual Peacham Fall Foliage Day: October 2 , 2025. If you can pull this off - do it!

Dining:

Peacham Café: Think scones, slow-roasted coffee, and farm-fresh everything. This is a community supported enterprise and the heart of town

Where to Stay: This is probably a clue as to why this town remains so picture perfect as there are not many places to stay. You are close to a plethora of choices along Interstate 91. For a dream destination, try the Rabbit Hill Inn. This adult only luxury boutique in has won numerous awards and is about 20 miles east.

Or head to your next destination - Woodstock, VT.

3: Woodstock

This town wears its history and fall as a favorite sweater. Covered bridges crisscross gentle rivers, grand inns hug the green, and every window glows at dusk. Side streets beckon with boutiques, while just outside of town, rolling farms and mountain hikes await.

4: Grafton

Grafton feels like a gentle exhale. White clapboard buildings, a winding village street, and the friendly greetings of shopkeepers set the tone. Beyond its storybook looks, this town is known for artistry, hearty cuisine, and a deep reverence for nature’s rhythms.

On Arrival & Nearby:

Stroll the picturesque lanes, pop into art galleries, and admire the restored homes and historic church steeples—then head to Grafton Trails & Outdoor Center for hiking, biking, or—in autumn—leaf-crunching rambling.

Shops:

MKT: Grafton: Delightfully curated market for gifts, gourmet treats, and everyday delights.
Grafton Village Cheese Company: Award-winning cheddar and local specialties.
The Mercantile at MKT: Home goods and artisan finds.

Dining:

MKT: Grafton: Breakfast sandwiches, pressed paninis, mac & cheese, and craft beer.
Phelps Barn Pub & 1801 Tavern at the Grafton Inn: Pub fare, Vermont beers, rustic barn ambiance, and autumn live music.

Where to Stay:

Grafton Inn: Historic, art-filled, and at the heart of the village.
Windham Hill Inn: Boutique tranquility just outside the village, broad lawns and mountain views.

5: Manchester & Dorset

Manchester is where refined taste meets small-town ease—lined with designer outlets, charming bookstores, and the historic grandeur of the Lincoln family estate. Dorset sparkles with marble sidewalks, artsy energy, and welcoming green.

Things to do:

Hildene—The Lincoln Family Home: Visit the mansion, gardens, farm, animal barns, and picnic by the Battenkill River. The views from this historic home are amazing!
Lye Brook Falls Trail: One of Vermont’s tallest waterfalls.
Equinox Mountain Skyline Drive: Drive up for panoramic Green Mountain views.
Manchester Designer Outlets: Outdoor, walkable, and home to upscale and local brands.
Northshire Bookstore: A magical haven for book lovers of all ages.
Southern Vermont Arts Center: Stroll the sculpture gardens, view creative exhibitions. Enjoy Curaté, the eaterie in the Arts Center.
Land Rover Experience Vermont: If you are a Land Rover lover, this is a fun, curated experience.

Dorset Charms:

Dorset Union Store: This is the real deal. The ready made food here is amazing with local eats, along with a wine selection that is perfect for crisp fall days.
Dorset Theatre Festival: Enjoy a play in a beautifully restored space. Truly, one of a kind. Get a ticket.

Dining:

Manchester

Silver Fork: Cozy inside a former library, acclaimed globally for its eclectic cuisine.
The Copper Grouse: Stylish, farm-to-table, bustling bar.
Seasons Restaurant: Casual, creative, locally-loved.

Dorset

Dorset Bakery: A block off the square, grab a hot cup of coffee and breakfast and bakery delights.
Dorset Tavern Restaurant: Breakfast and dinner at this long established restaurant is the thing of generations. Grab a perfect cocktail after the theater at the cozy bar.
Barrows House Restaurant: This American gastro-pub welcomes you with fresh takes on the most current offerings. Don’t miss Chef Zach’s magic touch for dinner or cocktails.

Stay:

Kimpton Taconic Hotel: Modern boutique, mountain views, dog-friendly.
The Dorset Inn: Vermont’s oldest inn, elegantly restored.
Barrows House Inn: Historic in a village setting, with on-site tavern.

6. Middlebury

Middlebury is a college town with a creative heart. The patchwork of historic stone buildings, waterfalls, and maple-dusted bakeries set beside the Green Mountains, make it picture perfect yet young and optimistic. It’s alive with academic energy, charm, and the arts.

Around Town & Beyond:

Middlebury College: Meander through classic collegiate quads lined with autumn maples.
Trail Around Middlebury (TAM): Hike a portion of this 19-mile loop.
Otter Creek Brewing: Tour and tastings at Vermont’s beer pioneer.

Shopping:

Maple Landmark: Vermont’s famous wooden toys and games.
Sweet Cecily: Gifts, locally made jewelry, lovely for browsing.

Dining:

Two Brothers Tavern: Lively basement spot for comfort food and Vermont beers.
The Arcadian: Rustic Italian, warm and inviting.
Otter Creek Bakery: Pastries, breads, and breakfast on the go.

Stay:

Swift House Inn: Refined, gardens, and a celebrated breakfast.

Burlington

If you are not heading right to the airport, Burlington is ready to send you off with a bit of big-small-town flair— Church Street’s buzz, Lake Champlain’s open horizon, and a creative undercurrent that draws in artists and adventurers alike. Its a sweet way to ease you back into big city life. Until next time.

Explore:

Burlington Bike Path/Greenway: Miles of lakeside biking and strolling.
Shelburne Farms: Historic farm estate, cheese tasting, sweeping water views.
Church Street Marketplace: Open-air, people-watching paradise, lined with shops and street performers.
Foam Brewers: Lakefront brewery pouring Vermont’s innovative craft beers.