55 days in Connecticut Itinerary

55 days in Connecticut Itinerary

Created using Inspirock Connecticut trip planner

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Route & dates

55 days in Connecticut Itinerary

Start: Boston
Drive:  1​h 45​min
1
Hartford
— 11 nights
Drive:  1​h 30​min
2
Kent
— 13 nights
Drive:  1​h 15​min
3
Norwalk
— 14 nights
Drive:  2​h 30​min
4
Mystic
— 16 nights
train:  1​h 45​min
End: Boston

11
nights
Hartford

Hartford ©
Hartford is the capital of the U.S. Explore Hartford's surroundings by going to Hubbard Park (in Meriden), Sleeping Giant State Park (in Hamden) and Gouveia Vineyards (in Wallingford). Next up on the itinerary: explore the galleries of The Mark Twain House & Museum, hike along Shenipsit Lake Trail - Blue Blazed, engage your brain at Connecticut Science Center, and explore the world behind art at New Britain Museum of American Art.

For where to stay, traveler tips, photos, and other tourist information, you can read our Hartford route planning website .

Boston to Hartford is an approximately 2-hour car ride. You can also take a bus; or take a train. In April, daytime highs in Hartford are 59°F, while nighttime lows are 39°F. Finish up your sightseeing early on the 18th (Thu) so you can go by car to Kent.

Things to do in Hartford

Parks Museums Outdoors

Side Trips

West Hartford, Windsor Locks, Newington, New Britain, East Hartford
Highlights from your plan
The Mark Twain House & Museum ©
The Mark Twain House & Museum
Wadsworth Atheneum Museum of Art ©
Wadsworth Atheneum Museum of Art
Connecticut Science Center ©
Connecticut Science Center

13
nights
Kent

Kent ©
Kent is a town in Litchfield County, Connecticut, alongside the border with New York. Change things up with these side-trips from Kent: West Cornwall Covered Bridge (in West Cornwall), Lime Rock Park (in Lakeville) and Sharon Audubon Center (in Sharon). There's still lots to do: get engrossed in the history at Hotchkiss-Fyler House Museum, contemplate the waterfront views at Candlewood Lake, examine the collection at Connecticut Antique Machinery, and contemplate in the serene atmosphere at Our Lady of Lourdes' Shrine.

For reviews, traveler tips, more things to do, and tourist information, refer to the Kent planner .

Traveling by car from Hartford to Kent takes 1.5 hours. April in Kent sees daily highs of 61°F and lows of 37°F at night. Finish up your sightseeing early on the 1st (Wed) so you can go by car to Norwalk.

Things to do in Kent

Parks Nature Museums

Side Trips

Litchfield, Washington, New Milford, Bethlehem, Norfolk
Highlights from your plan
Kent Falls State Park ©
Kent Falls State Park
Connecticut Antique Machinery ©
Connecticut Antique Machinery
Bull's Bridge ©
Bull's Bridge

14
nights
Norwalk

Norwalk ©
Norwalk, is the sixth most populous city in the U.S. Explore the numerous day-trip ideas around Norwalk: Stratford (Two Roads Brewing Company & Lordship Seawall), New Haven (Yale Peabody Museum of Natural History, St. Mary's Church, & more) and Fairfield (Fairfield University Art Museum & Lake Mohegan Recreation Area). There's lots more to do: take a peaceful walk through Gurski Farm- Williams Park, make a trip to Flinn Gallery, admire the majestic nature at Collis P. Huntington State Park, and meet the residents at The Maritime Aquarium.

For reviews, photos, other places to visit, and more tourist information, go to the Norwalk holiday planner.

You can drive from Kent to Norwalk in 1.5 hours. In May, plan for daily highs up to 69°F, and evening lows to 52°F. Wrap up your sightseeing on the 15th (Wed) early enough to travel to Mystic.

Things to do in Norwalk

Parks Museums Nature

Side Trips

New Haven, New Canaan, Stamford, Fairfield, Greenwich
Highlights from your plan
Silver Sands State Park ©
Silver Sands State Park
Yale University Art Gallery ©
Yale University Art Gallery
Stepping Stones Museum for Children ©

16
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Venture out of the city with trips to Waterford Beach Park (in Waterford), East Haddam (Ray of Light Farm & Gillette Castle State Park) and Madison (Hammonasset Beach State Park, Meigs Point Nature Center, & more). Pack the 23rd (Thu) with family-friendly diversions at The Dinosaur Place at Nature's Art Village. And it doesn't end there: meet the residents at Mystic Aquarium, take in the pleasant sights at Mystic River Historical Society, examine the collection at The Submarine Force Museum, and take an in-depth tour of Mashantucket Pequot Museum & Research Center.

To find reviews, more things to do, ratings, and more tourist information, you can read our Mystic trip itinerary tool .

Traveling by car from Norwalk to Mystic takes 1.5 hours. In May, plan for daily highs up to 65°F, and evening lows to 48°F. Wrap up your sightseeing on the 31st (Fri) early enough to take a train back home.

Things to do in Mystic

Parks Museums Historic Sites

Side Trips

Groton, New London, Madison, Stonington, Mashantucket
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum
Mystic Aquarium ©
Mystic Aquarium
Olde Mistick Village ©
Olde Mistick Village

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