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
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Simsbury
— 11 nights
Drive
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Washington
— 11 nights
Drive

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New Haven — 10 nights

Change things up with these side-trips from New Haven: New Britain Museum of American Art (in New Britain), Panthorn Park (in Plantsville) and Still Hill Brewery (in Rocky Hill).

To see photos, ratings, where to stay, and other tourist information, read our New Haven sightseeing planner.

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 up your sightseeing early on the 19th (Tue) so you can go by car to Mystic.
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Parks · Museums · Historic Sites · Breweries & Distilleries
Side Trips

Mystic — 10 nights

Change things up with these side-trips from Mystic: Niantic Bay Boardwalk (in East Lyme), Essex (Main Street Park, Essex Village & Essex Library Association) and East Haddam (Ray of Light Farm, Gillette Castle State Park, &more). The adventure continues: get engrossed in the history at Mystic Seaport Museum, try to win big at Foxwoods Resort Casino, step aboard Charles W. Morgan, and contemplate the long history of Olde Mistick Village.

To see reviews, where to stay, photos, and tourist information, read Mystic trip planning website.

You can drive from New Haven to Mystic in an hour. Another option is to take a train. November in Mystic sees daily highs of 54°F and lows of 37°F at night. Finish your sightseeing early on the 29th (Fri) to allow enough time to drive to Woodstock.
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Parks · Museums · Historic Sites · Nature
Side Trips

Woodstock — 10 nights

Explore the numerous day-trip ideas around Woodstock: The Lodge at Crandall Park (in Tolland), Stafford Library (in Stafford) and Gay City State Park (in Hebron).

To see maps, more things to do, ratings, and other tourist information, you can read our Woodstock tour itinerary planner.

Traveling by car from Mystic to Woodstock takes 1.5 hours. Traveling from Mystic in November, you can expect nighttime temperatures to be slightly colder in Woodstock, with lows of 32°F. Finish your sightseeing early on the 9th (Mon) to allow enough time to drive to Simsbury.
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Parks · Outdoors · Trails · Nature
Side Trips

Simsbury — 11 nights

Simsbury is known for trails, sightseeing, and wineries. Your trip includes some of its best attractions: don't miss a visit to Heublein Tower, indulge your thirst for a good beer at Thomas Hooker Brewery, identify plant and animal life at McLean Game Refuge, and explore the landscape on two wheels at Farmington Canal Heritage Trail.

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 drive to Washington.
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Outdoors · Parks · Trails · Historic Sites
Side Trips

Washington — 11 nights

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).

For maps, photos, reviews, and more tourist information, read Washington sightseeing planning site.

Getting from Simsbury to Washington by car takes about 1.5 hours. Expect a daytime high around 41°F in December, and nighttime lows around 28°F. On the 31st (Tue), wrap the sightseeing up by early afternoon so you can drive back home.
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Parks · Museums · Nature · Wildlife
Side Trips

Connecticut travel guide

4.3
History Museums · Historic Sites · Aquariums
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.
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