53 days in Connecticut Itinerary

53 days in Connecticut Itinerary

Created using Inspirock Connecticut trip planner

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Make it your trip
Drive
1
New Haven
— 10 nights
Drive
2
Mystic
— 10 nights
Drive
3
Woodstock
— 10 nights
Drive
4
Simsbury
— 11 nights
Drive
5
Washington
— 11 nights
Drive

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New Haven

— 10 nights
New Haven, in the U.S. state of Connecticut, is the principal municipality in Greater New Haven, which had a total population of 862,477 in 2010. Change things up with these side-trips from New Haven: Still Hill Brewery (in Rocky Hill), New Britain Museum of American Art (in New Britain) and Panthorn Park (in Plantsville). There's much more to do: admire the masterpieces at Yale University Art Gallery, observe the fascinating underwater world at The Maritime Aquarium, contemplate the long history of New Haven Railroad Station, and get lost in a book at Beinecke Rare Book & Manuscript Library.

To see more things to do, photos, and tourist information, go to the New Haven trip itinerary maker app.

Newark to New Haven is an approximately 2-hour car ride. You can also take a train; or take a bus. November in New Haven sees daily highs of 53°F and lows of 36°F at night. Finish your sightseeing early on the 19th (Tue) so you can drive to Mystic.

Things to do in New Haven

Parks · Museums · Historic Sites · Breweries & Distilleries

Side Trips

Mystic

— 10 nights
A historical leading seaport, Mystic has maintained a strong respect for the past.
Change things up with these side-trips from Mystic: Essex (Main Street Park, Essex Village & Essex Library Association), East Haddam (Ray of Light Farm, Gillette Castle State Park, &more) and Niantic Bay Boardwalk (in East Lyme). The adventure continues: observe the fascinating underwater world at Mystic Aquarium, step aboard Charles W. Morgan, don't miss a visit to Mystic & Shoreline Visitor Information Center, and snap pictures at Mystic River Bascule Bridge.

To see reviews, more things to do, ratings, and other tourist information, go to the Mystic online vacation planner.

Traveling by car from New Haven to Mystic takes an hour. Alternatively, you can take a train. In November, daily temperatures in Mystic can reach 54°F, while at night they dip to 37°F. Wrap up your sightseeing on the 29th (Fri) to allow time to drive to Woodstock.

Things to do in Mystic

Parks · Museums · Historic Sites · Nature

Side Trips

Woodstock

— 10 nights
Woodstock is a town in Windham County, Connecticut, United States. Explore the numerous day-trip ideas around Woodstock: The Lodge at Crandall Park (in Tolland), Gay City State Park (in Hebron) and Stafford Library (in Stafford). There's lots more to do: do a tasting at Taylor Brooke Winery, get lost in a book at The Wood Memorial Library & Museum, walk around Northwest Park, and take your sightseeing to a higher altitude at Case Mountain.

To see traveler tips, maps, where to stay, and tourist information, read Woodstock itinerary planner.

You can drive from Mystic to Woodstock in 1.5 hours. Traveling from Mystic in November, plan for a bit cooler nights in Woodstock, with lows around 32°F. Finish your sightseeing early on the 9th (Mon) to allow enough time to travel to Simsbury.

Things to do in Woodstock

Parks · Outdoors · Trails · Nature

Side Trips

Simsbury

— 11 nights
Simsbury is an affluent town in Hartford County, Connecticut, United States. Simsbury is known for trails, wineries, and classes. Your plan includes some of its best attractions: don't miss a visit to Heublein Tower, hike along West Hartford Reservoir, learn about winemaking at Lost Acres Vineyard, and stop by The Blue House: Nice Old Things and The Junk Shop.

For photos, more things to do, and tourist information, read our Simsbury road trip planning site.

You can drive from Woodstock to Simsbury in 1.5 hours. In December, daily temperatures in Simsbury can reach 42°F, while at night they dip to 27°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to travel to Washington.

Things to do in Simsbury

Outdoors · Parks · Trails · Historic Sites

Side Trips

Washington

— 11 nights
Washington is a rural town in Litchfield County, Connecticut, in the New England region of the United States. Explore Washington's surroundings by going to Lime Rock Park (in Lakeville), Campbell Falls State Park (in Norfolk) and Beckley Furnace Industrial Monument (in East Canaan). And it doesn't end there: identify plant and animal life at Steep Rock Preserve, take in nature's colorful creations at Hollister House Garden, trek along Tarrywile Park & Mansion, and examine the collection at Gunn Historical Museum.

For where to stay and tourist information, read our Washington travel route builder site.

You can drive from Simsbury to Washington in 1.5 hours. Expect a daytime high around 41°F in December, and nighttime lows around 28°F. Wrap up your sightseeing by early afternoon on the 31st (Tue) to allow enough time to travel back home.

Things to do in Washington

Parks · Museums · Nature · Wildlife

Side Trips

Connecticut travel guide

4.3
Historic Sites · Aquariums · Theaters
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.