15 days in Vermont Itinerary

15 days in Vermont Itinerary

Created using Inspirock United States Trip Planner

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Route & dates

15 days in Vermont Itinerary

Start: New York City
Fly:  3​h 45​min
1
Burlington
— 4 nights
Drive:  1​h 15​min
2
Middlebury
— 2 nights
Drive:  1​h 15​min
3
Berlin
— 2 nights
Drive:  1​h 15​min
4
Woodstock
— 4 nights
Drive:  1​h 45​min
5
Manchester
— 2 nights
Drive:  4​h 15​min
End: New York City


4
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Take a break from the city and head to North Beach Park and Waterskiing & Jetskiing. Eschew the tourist crowds and head to Boyden Valley Winery and University of Vermont. Change things up with a short trip to Mt. Philo State Park in Charlotte (about 34 minutes away). And it doesn't end there: take a memorable tour with Tours, sample the tasty concoctions at Switchback Brewing, learn about winemaking at Beverage Warehouse, and go for a stroll along the water at Burlington Community Boathouse Marina.

For where to stay, traveler tips, ratings, and other tourist information, you can read our Burlington vacation trip planner.

New York City to Burlington is an approximately 4-hour flight. You can also drive; or take a bus. Expect slightly colder temperatures when traveling from New York City in August; daily highs in Burlington reach 80°F and lows reach 60°F. Wrap up your sightseeing on the 8th (Tue) early enough to travel to Middlebury.

Things to do in Burlington

Parks Wineries Outdoors

Side Trips

Shelburne, Beverage Warehouse, Mt. Philo State Park, Boyden Valley Winery
Find places to stay Aug 4 — 8:
Highlights from your plan
Mt. Philo State Park ©
Mt. Philo State Park
Boyden Valley Winery ©
Boyden Valley Winery
Switchback Brewing ©
Switchback Brewing

2
nights
Middlebury

Middlebury ©
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. On the 8th (Tue), experience rural life at Dakin Farm and then hike along Robert Frost Wayside Trail. Keep things going the next day: stop by Danforth Pewter, sample the tasty concoctions at Otter Creek Brewing Company, then indulge your thirst for a good beer at Woodchuck Cider House, and finally relax in the rural setting at UVM Morgan Horse Farm.

To find traveler tips, ratings, photos, and other tourist information, read Middlebury tour planner.

Drive from Burlington to Middlebury in an hour. Expect a daytime high around 78°F in August, and nighttime lows around 57°F. Finish your sightseeing early on the 10th (Thu) so you can travel to Berlin.

Things to do in Middlebury

Outdoors Breweries Parks

Side Trips

Robert Frost Wayside Trail, Dakin Farm, Woodchuck Cider House
Find places to stay Aug 8 — 10:
Highlights from your plan
Dakin Farm ©
Dakin Farm
Woodchuck Cider House ©
Woodchuck Cider House
Otter Creek Brewing ©
Otter Creek Brewing

2
nights
Berlin

Berlin ©
Berlin is a town in Worcester County, Maryland, United States which includes its own historical Berlin Commercial District. Kick off your visit on the 10th (Thu): explore the different monuments and memorials at Hope Cemetery, then look for gifts at Laughing Moon Chocolates, and then take in the dramatic scenery at Moss Glen Falls. On the next day, don't miss a visit to Bragg Farm Sugar House & Gift, then soothe aching muscles at some of the top local wellness centers, and then admire all the interesting features of Toll Rd.

For more things to do, maps, photos, and other tourist information, refer to the Berlin custom trip planner.

Drive from Middlebury to Berlin in 1.5 hours. In August in Berlin, expect temperatures between 77°F during the day and 55°F at night. Finish your sightseeing early on the 12th (Sat) to allow enough time to travel to Woodstock.

Things to do in Berlin

Parks Outdoors Scenic Drive

Side Trips

Stowe, Hope Cemetery, Bragg Farm Sugar House & Gift Shop
Find places to stay Aug 10 — 12:
Highlights from your plan
Moss Glen Falls ©
Moss Glen Falls
Spas & Wellness
Bragg Farm Sugar House & Gift Shop ©
Bragg Farm Sugar House & Gift Shop

4
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Visiting Thundering Falls Trail and Mount Tom will get you outdoors. You'll discover tucked-away gems like Kayaking & Canoeing and President Calvin Coolidge State Historic Site. Go for a jaunt from Woodstock to Ludlow to see Buttermilk Falls about 40 minutes away. There's still lots to do: contemplate the waterfront views at Ottaquechee River, browse the different shops at Quechee Gorge Village Vermont Antique Mall, indulge your thirst for a good beer at Long Trail Brewing Company, and snap pictures at Cornish-Windsor Bridge.

To see reviews, traveler tips, and more tourist information, you can read our Woodstock itinerary planner.

You can drive from Berlin to Woodstock in an hour. In August, plan for daily highs up to 81°F, and evening lows to 56°F. Wrap up your sightseeing on the 16th (Wed) to allow time to drive to Manchester.

Things to do in Woodstock

Parks Nature Outdoors

Side Trips

Montshire Museum of Science, Quechee Gorge Village Vermont Antique Mall, Thundering Falls Trail, Cornish-Windsor Bridge, Long Trail Brewing Company
Find places to stay Aug 12 — 16:
Highlights from your plan
Ottaquechee River ©
Ottaquechee River
Montshire Museum of Science ©
Montshire Museum of Science
Long Trail Brewing Company ©
Long Trail Brewing Company

2
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Visiting Equinox Mountain and Lye Brook Falls will get you outdoors. Eschew the tourist crowds and head to Equinox Preservation Trust and Northshire Bookstore. Explore the numerous day-trip ideas around Manchester: Bennington (The Old First Church & Silk Road Covered Bridge) and Wilmington (Adams Farm, The Art of Humor Gallery, & more).

For traveler tips, maps, photos, and other tourist information, read our Manchester itinerary builder.

You can drive from Woodstock to Manchester in 2 hours. Another option is to take a bus. In August, plan for daily highs up to 79°F, and evening lows to 55°F. Finish up your sightseeing early on the 18th (Fri) so you can go by car back home.

Things to do in Manchester

Parks Nature Wildlife

Side Trips

Wilmington, Bennington, Equinox Mountain
Find places to stay Aug 16 — 18:
Highlights from your plan
Equinox Mountain ©
Equinox Mountain
Adams Farm ©
Adams Farm
Harriman Reservoir ©
Harriman Reservoir

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