15 days in Vermont Itinerary

15 days in Vermont Itinerary

Created using Inspirock Vermont route builder

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Route & dates

15 days in Vermont Itinerary

Start: Boston
Fly:  2​h 30​min
1
Woodstock
— 3 nights
Drive:  1​h 30​min
2
Saint Johnsbury
— 4 nights
Drive:  1​h 45​min
3
Shelburne
— 3 nights
Drive:  2​h 30​min
4
Bennington
— 4 nights
Drive:  3​h 15​min
End: Boston

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Venture out of the city with trips to Okemo Mountain Resort (in Ludlow), Deer Leap Trail (in Rutland) and Killington Resort (in Killington). Next up on the itinerary: relax in the rural setting at Sugarbush Farm, engage your brain at Montshire Museum of Science, take in the awesome beauty at Mount Tom, and explore the stunning scenery at Quechee Gorge.

To find traveler tips, more things to do, maps, and other tourist information, go to the Woodstock online sightseeing planner .

Boston to Woodstock is an approximately 2.5-hour flight. You can also drive; or take a bus. Plan for slightly colder nights when traveling from Boston in May since evenings lows in Woodstock dip to 45°F. Finish up your sightseeing early on the 28th (Thu) so you can go by car to Saint Johnsbury.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

Quechee, Killington Resort, Deer Leap Trail, Montshire Museum of Science, Okemo Mountain Resort
Find places to stay May 25 — 28:
Highlights from your plan
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum

4
nights
Saint Johnsbury

Saint Johnsbury ©
St. Venture out of the city with trips to Jay Peak Pump House (in Jay), Barre (Rock of Ages Granite Quarry & Hope Cemetery) and Lake Willoughby (in East Burke). And it doesn't end there: stroll around Dog Mountain Home of Stephen Huneck Gallery, see the interesting displays at Fairbanks Museum and Planetarium, admire the landmark architecture of The Dog Chapel, and take in the views from Sunset Lake Floating Bridge.

For photos, reviews, other places to visit, and tourist information, you can read our Saint Johnsbury route builder website .

Drive from Woodstock to Saint Johnsbury in 1.5 hours. In May, daily temperatures in Saint Johnsbury can reach 68°F, while at night they dip to 44°F. Wrap up your sightseeing on the 1st (Mon) early enough to drive to Shelburne.

Things to do in Saint Johnsbury

Parks Museums Nature

Side Trips

Barre, Montpelier, Green Mountain Distillers, Sunset Lake Floating Bridge, Lake Willoughby
Find places to stay May 28 — Jun 1:
Highlights from your plan
St. Johnsbury Athenaeum ©
St. Johnsbury Athenaeum
Fairbanks Museum and Planetarium ©

3
nights
Shelburne

Shelburne ©
Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. Get out of town with these interesting Shelburne side-trips: Stowe (Stowe Recreation Path & Mount Mansfield State Forest) and Beer Tastings & Tours (in Burlington). There's still lots to do: see the interesting displays at Shelburne Museum, look for gifts at Lake Champlain Chocolates, browse the eclectic array of goods at Church Street Marketplace, and stroll through Burlington Bike Path.

To see photos, ratings, reviews, and more tourist information, refer to the Shelburne day trip app .

Drive from Saint Johnsbury to Shelburne in 2 hours. In June, plan for daily highs up to 77°F, and evening lows to 57°F. Wrap up your sightseeing on the 4th (Thu) to allow time to travel to Bennington.

Things to do in Shelburne

Parks Trails Outdoors

Side Trips

Burlington, Stowe, Magic Hat Brewing Company
Find places to stay Jun 1 — 4:
Highlights from your plan
Shelburne Museum ©
Shelburne Museum
Shelburne Farms ©
Shelburne Farms
Stowe Recreation Path ©
Stowe Recreation Path

4
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Explore Bennington's surroundings by going to Bromley Mountain (in Peru), Manchester (Hildene, The Lincoln Family Home & North Meadow Farm) and Mount Snow Resort (in Dover). There's much more to do: pause for some photo ops at Bennington Battle Monument, sample the fine beverages at Saxtons Distillery, don't miss a visit to Jim McGrath Gallery and Studio, and stroll the grounds of The Old First Church.

To find out how to plan a trip to Bennington, use our trip itinerary maker.

Drive from Shelburne to Bennington in 2.5 hours. Expect a daytime high around 76°F in June, and nighttime lows around 53°F. Finish your sightseeing early on the 8th (Mon) so you can travel back home.

Things to do in Bennington

Parks Winter Sports Historic Sites

Side Trips

Manchester, Brattleboro, Putney, Vermont Country Store, Jim McGrath Gallery and Studio
Find places to stay Jun 4 — 8:
Highlights from your plan
Hildene, The Lincoln Family Home ©
Bennington Battle Monument ©
Bennington Battle Monument
Bennington Museum ©
Bennington Museum

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