11 days in Vermont Itinerary

11 days in Vermont Itinerary

Created using Inspirock Vermont Trip Planner

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Make it your trip
Drive
1
Bennington
— 2 nights
Drive
2
Killington
— 2 nights
Drive
3
Berlin
— 3 nights
Drive
4
Winooski
— 3 nights
Drive

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Bennington

— 2 nights
Bennington is a town in Bennington County, Vermont, in the United States. Kick off your visit on the 30th (Sat): stroll the grounds of New Catholic Cemetery and then explore the different monuments and memorials at The Old First Church. Here are some ideas for day two: look for all kinds of wild species at Equinox Preservation Trust and then admire the sheer force of Lye Brook Falls.

For maps, ratings, more things to do, and other tourist information, read Bennington route planning website.

New York City to Bennington is an approximately 3.5-hour car ride. You can also take a bus; or do a combination of train and bus. In September, Bennington is slightly colder than New York City - with highs of 74°F and lows of 48°F. Finish up your sightseeing early on the 2nd (Mon) so you can go by car to Killington.

Things to do in Bennington

Parks · Wildlife · Historic Sites · Nature

Side Trip

Killington

— 2 nights
Killington is a town in Rutland County, Vermont, United States. Explore hidden gems such as Woodchuck Cider House and Green Mountain Sugar House. When in Killington, make a side trip to see Otter Creek Brewing in Middlebury, approximately Middlebury away. Next up on the itinerary: sample the tasty concoctions at Long Trail Brewing Company, hike along Thundering Falls Trail, steep yourself in history at Calvin Coolidge Homestead, and contemplate the waterfront views at Ottaquechee River.

To find where to stay, other places to visit, photos, and tourist information, refer to the Killington itinerary planner.

You can drive from Bennington to Killington in 1.5 hours. Expect a daytime high around 60°F in October, and nighttime lows around 42°F. Wrap up your sightseeing on the 4th (Wed) early enough to travel to Berlin.

Things to do in Killington

Parks · Breweries & Distilleries · Outdoors · Trails

Side Trips

Berlin

— 3 nights
Berlin is a town in Washington County, Vermont, United States, founded in 1763.The population was 2,887 at the 2010 census. Kick off your visit on the 5th (Thu): stroll the grounds of Hope Cemetery, take in the exciting artwork at Ziemke Glass Blowing Studio, and then snap pictures at Gold Brook Covered Bridge (Emily's Covered Bridge). Here are some ideas for day two: sample the tasty concoctions at Rock Art Brewery, then take in the dramatic scenery at Moss Glen Falls, and then look for gifts at Craft Beer Cellar.

To find where to stay, reviews, maps, and tourist information, you can read our Berlin day trip planner.

Traveling by car from Killington to Berlin takes 1.5 hours. In October, daily temperatures in Berlin can reach 58°F, while at night they dip to 38°F. Finish your sightseeing early on the 7th (Sat) so you can travel to Winooski.

Things to do in Berlin

Parks · Nature · Shopping · Breweries & Distilleries

Side Trips

Winooski

— 3 nights
Winooski is a city in Chittenden County, Vermont, United States. Your inner history buff will appreciate St. Anne's Shrine and Round Church. You'll explore the less-touristy side of things at Beverage Warehouse and Switchback Brewing. Step out of Winooski with an excursion to Boyden Valley Winery & Spirits in Cambridge--about 40 minutes away. Next up on the itinerary: stop by The Shelburne Country Store, learn about winemaking at Shelburne Vineyard, don't miss a visit to World's Tallest Filing Cabinet, and gain insight at University of Vermont.

To find ratings, traveler tips, other places to visit, and other tourist information, read Winooski travel route planner.

Traveling by car from Berlin to Winooski takes an hour. Traveling from Berlin in October, plan for somewhat warmer nights in Winooski, with lows around 44°F. Wrap up your sightseeing on the 10th (Tue) early enough to travel back home.

Things to do in Winooski

Wineries · Parks · Historic Sites · Beaches

Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Hiking Trails
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.