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Create Your Vermont Itinerary

As you plan your Vermont vacation, itineraries can help you make the most of your experience. Whether you’re planning a weekend getaway or a week-long immersive trip, your days in Vermont can be as full or unplanned as you like. Itineraries featuring accessible adventure, historic downtowns, outdoor recreation, and Vermont’s unique regions make great starting points as you plan your trip.

What Do You Do with Three Days in Vermont?

There’s a lot you can do with just three days in Vermont. Whether you’re planning a slow, restorative long weekend or snapping up midweek openings to experience the Green Mountain State, these regional guides will inspire you to see what’s out there and venture off the beaten path for yourself.

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72 Hours in Bennington

Vermont’s Shires region is a stronghold of arts, history, culture, and things to do, as well as access to bountiful outdoor recreation options. Here’s how to spend 72 hours in Bennington.

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72 Hours in the Woodstock-Quechee Region

Located along the eastern section of the Vermont Route 4 Scenic Byway, take in the history of the Woodstock-Quechee region while exploring, shopping, and dining.

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72 Hours in Vermont’s Northeast Kingdom

One of the most awe-inspiring destinations in Vermont, this regional itinerary will have you feeling like a local. Venture to the Canadian border or find a touch of big-city flair in a small town.

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72 Hours in St Albans

Located at the northeastern end of Lake Champlain, St. Albans offers visitors a little bit of everything. Find a rich history in this charming downtown that has largely been unchanged since the mid-1800’s.

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72 Hours in Norwich

Located in the heart of the Upper Valley, Norwich is the quintessential New England village. Follow this three-day itinerary to experience all the history and charm that’s packed into this quaint town.

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72 Hours in the Okemo Valley

Vermont’s Scenic Route 100 Byway winds across the Okemo Valley, through small villages that offer outdoor concerts and miles of backcountry. Here’s how to spend three days along the byway.

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72 Hours in Greater Burlington

Find recreation paths along a coastal-inspired town and explore historically significant Americana in an outdoor museum. On Burlington’s waterfront, immerse yourself in the vibrant arts scene and sunsets over Lake Champlain.

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Hit the road with Mirna

Endurance athlete and Vermonter Mirna Valerio, a.k.a. “The Mirnavator,” loves to explore all over the Green Mountain State. Join Mirna on her adventures to discover hidden Vermont gems, vibrant downtowns, and local flavors.

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Things to do in Vermont’s Downtowns

Vermont’s historic downtowns are cultural and culinary hubs for your Vermont vacation. The articles below offer inspiration for things to do in and around each downtown.

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Things to Do in Middlebury

The college town of Middlebury welcomes with literary history, contemporary art, and a historic and walkable downtown. Here’s what to see, do, and eat there.

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Things to Do in Springfield

This southern Vermont town is the official Springfield of “The Simpsons Movie.” It’s home to American manufacturing history, a short rail trail, and the oldest one-room schoolhouse in Vermont.

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Things to Do in Rutland

The state’s third-largest city has a lot to offer visitors, from the Vermont State Fair to the restored Paramount Theatre and a lot of local dining in between.

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Things to Do in Winooski

Among the smallest cities in Vermont, Winooski is home to a diverse culture, which echoes through the streets as music and livens local menus citywide. This itinerary includes a mill museum, a Wednesday outdoor celebration, and more.

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Things to Do in the Champlain Islands

Discover Vermont’s very own fossil reef, a bike path that stretches across Lake Champlain, five state parks, and 200 miles of shoreline in Vermont’s Champlain Islands.

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Things to Do in Montpelier

Montpelier is the country’s smallest state capital. See one of the nation’s oldest continuously operating state houses, an array of locally owned stores and restaurants, and some of Vermont’s finest crafts.

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Things to Do in St Johnsbury

Vermont’s only public planetarium, a chapel and trails dedicated to dogs, rural Northeast Kingdom setting, and world-class craft brewing set St. Johnsbury apart. Here’s what to see, do, and eat there.

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Things to Do in Vergennes

Vergennes is Vermont’s first official city, home to a harborfront family resort, a museum celebrating Lake Champlain’s history, historic brick buildings in a quaint downtown, and local shopping and dining galore.

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Things to Do in Bristol

Historic downtown Bristol is quiet – but there’s plenty going on, from a locally beloved swimming hole to eclectic downtown shopping and a short hike with sweeping views of the Green Mountains.

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Things to Do in Poultney

In the heart of the Stone Valley, Poultney is home to Lake St. Catherine, a year-round recreation destination, some of the state’s earliest quarrying history, a local vineyard, and a 20-mile rail trail.

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Things to Do in Shelburne

From a massive collection of art and Americana on a sprawling outdoor museum to independent shops, a historic country store, and more, Shelburne’s got lots to see. Here’s what to see, do, and eat there.

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Things to Do in Brandon

Brandon lives up to its nickname: The Art and Soul of Vermont. With an entire downtown core listed on the National Register of Historic Places, world-renowned artists nearby, and hundreds of acres of outdoor recreation, there’s lots to see, do, and eat.

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Things to Do in Windsor

Called the Birthplace of Vermont, Windsor is home to a manufacturing museum, a classic 1950s-style lunch counter, and the longest covered bridge in the U.S. Here’s what to see, do, and eat there.

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Things to Do in Brattleboro

A historic collection of musical organs, a robust slate of festivals and programs, and a storied old church now housing a live music venue are just some of the highlights of a trip to Brattleboro.

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Things to Do in Burlington

Vermont’s largest city is home to the No. 1 public square in the U.S., a bike path that crosses Lake Champlain, and a vibrant culture centered around art and small businesses. Here’s what to see, do, and eat there.

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Things to Do in Bennington

In Bennington, discover still-lively Revolutionary War history, a festival celebrating garlic, a diner in an old train car, Vermont’s tallest man-made monument, and more. Here’s your itinerary for things to see, do, and eat in “the gateway to Vermont.”

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Things to Do in Randolph

In Vermont’s geographic center, discover standout brunch, a live theatre and music center for the arts, a historic movie theatre, and more along this itinerary.

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Things to Do in St Albans

On the shores of Lake Champlain, the city of St. Albans abounds with outdoor recreation, from a rail trail to a community ski hill to a public pool. Downtown, find local dining, brewing, and community events.

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Things to Do in Bellows Falls

Home to the state’s only national park, near its deepest gorge, and widely recognized as quaint, Woodstock is an idyllic Upper Valley destination for travelers seeking small-town charm.

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Things to Do in Woodstock

Home to the state’s only national park, near its deepest gorge, and widely recognized as quaint, Woodstock is an idyllic Upper Valley destination for travelers seeking small-town charm.

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Things to Do in Wilmington

An art gallery dedicated to humor, a classic diner, the largest body of water entirely within Vermont’s borders, and more are all on offer in Wilmington. Here’s what to see, do, and eat on your trip there.

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Things to Do in Barre

Barre is defined by a rich stone history, outdoor art that makes the whole downtown feel like a museum, and an eclectic mix of shopping and dining. This itinerary will point your way.

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Things to Do in Manchester

A longstanding Vermont destination, Manchester is home to the former summer home of the presidential Lincoln family, Vermont’s oldest inn, and a rich fly-fishing culture, as well as designer shops. Here’s what to see, do, and eat there.

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Things to Do in the Okemo Valley

A ski resort with more than 100 trails is the four-season star of Vermont’s Okemo Valley, but nearby, discover presidential history, a renowned classic country store, and a year-round theatre company.

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Things to Do in Waterbury

All-day local breakfast, a factory tour of Vermont’s most famous ice cream, and lots of local beer are all on the menu for a trip to Waterbury, Vermont.

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Things to Do in Hardwick

Hardwick is one of the Northeast Kingdom’s gems, with a focus on local dining, entry to the longest rail trail in New England, eclectic shopping, and more.

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Things to Do in Stowe

Home to Vermont’s tallest peak, with all the outdoor recreation that goes along with it, the von Trapp Family Lodge, a 5-mile paved path winding throughout downtown, and more, Stowe is a four-season destination.

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Things to Do in Newport and Jay

Vermont’s Northeast Kingdom is a bucolic three-county region that offers some of the most pristine pastoral vistas in Vermont; it’s also a hub for recreation of all kinds. Here are some highlights from Newport and Jay, two of the region’s 48 small towns.

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A person in a wheelchair seen from behind as they look at a waterfall view.

A person in a wheelchair on a boardwalk seen from behind moving along the trail in the summer.

An Itinerary for Every Body

Wheelchair-Accessible Vermont Adventure

Blogger and wheelchair user Cory Lee tours Vermont for a week of accessible adventure in the fall, from sampling maple syrup and seeing wild birds up close to taking in beautiful waterfall views on accessible trails.

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Itineraries by Train

Two Amtrak train lines connect Vermont to the rest of the country, stopping in walkable downtowns throughout the state. Explore Vermont’s historic downtowns on foot, bring your bike on the train, or rent a car to spend a long weekend in Vermont via rail.

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A Long Weekend in Burlington

A train trip to Burlington includes shopping and dining at Church Street Marketplace, named the nation’s No. 1 public square, Sunday brunch, and beautiful lake views.

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A Long Weekend in Vergennes

Travel by Amtrak to Vergennes for a weekend of bike riding, eating from-scratch ice cream, and spending time in nature at a state park.

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A Long Weekend in Middlebury

Take the train to Middlebury for a weekend of exploring local nature paths, art exhibits, and delicious eats.

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Your Outdoors Itinerary

How much world-class outdoor recreation can you fit into your time in Vermont? From hiking and biking to running, skiing, riding, paddling, and more, Vermont’s outdoor activities are almost limitless.

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Vermont’s Welcome Centers

Statewide, Vermont’s visitor centers are welcoming sights, offering information on lodging, dining, and recreation, along with restrooms and Wi-Fi. Many are in scenic settings themselves, such as historic train stations, veterans’ memorials, and more.

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