53 days in Connecticut Itinerary

53 days in Connecticut Itinerary

Created using Inspirock Connecticut trip planner

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Plan created by another user. Make it yours

Route & dates

1
New Haven
— 10 nights
2
Mystic
— 10 nights
3
Woodstock
— 10 nights
4
Simsbury
— 11 nights
5
Washington
— 11 nights

10
nights
New Haven

New Haven ©
New Haven, in the U.S. Change things up with these side-trips from New Haven: New Britain Museum of American Art (in New Britain), Still Hill Brewery (in Rocky Hill) and Panthorn Park (in Plantsville). There's lots more to do: explore the world behind art at Yale University Art Gallery, get up close and personal with brilliant marine life at The Maritime Aquarium, contemplate the long history of The Mark Twain House & Museum, and identify plant and animal life at A Place Called Hope.

For photos, maps, more things to do, and tourist information, go to the New Haven route builder site.

Newark to New Haven is an approximately 2-hour car ride. You can also take a train; or take a bus. In November, daytime highs in New Haven are °F, while nighttime lows are °F. Finish up your sightseeing early on the 19th (Tue) so you can go by car to Mystic.

Things to do in New Haven

Parks Museums Historic Sites

Side Trips

Hartford, New Canaan, Stratford, Greenwich, Stamford
Highlights from your plan
Yale University Art Gallery ©
Yale University Art Gallery
Yale Peabody Museum of Natural History ©
Yale Peabody Museum of Natural History
Yale University ©
Yale University

10
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Change things up with these side-trips from Mystic: East Haddam (Ray of Light Farm, Gillette Castle State Park, &more), Old Lyme (Sculpture Grounds & DEEP Marine Headquarters - Ferry Landing Park) and Essex (Main Street Park, Essex Village & Essex Library Association). The adventure continues: examine the collection 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. Other options are to take a train; or do a combination of bus and train. November in Mystic sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 29th (Fri) to allow enough time to drive to Woodstock.

Things to do in Mystic

Parks Museums Historic Sites

Side Trips

Groton, Waterford, East Haddam, Old Lyme, Norwich
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum
Mystic Aquarium ©
Mystic Aquarium
Olde Mistick Village ©
Olde Mistick Village

10
nights
Woodstock

Woodstock ©
Woodstock is a town in Windham County, Connecticut, United States. Explore the numerous day-trip ideas around Woodstock: Gay City State Park (in Hebron), The Lodge at Crandall Park (in Tolland) and Stafford Library (in Stafford). And it doesn't end there: learn about winemaking at Taylor Brooke Winery, stroll through Vernon Rails-to-Trails, contemplate the long history of Prudence Crandall Museum, and experience rural life at Woodstock Orchard.

To see ratings, other places to visit, more things to do, and other tourist information, use the Woodstock trip planning tool.

Getting from Mystic to Woodstock by car takes about 1.5 hours. Plan for a bit cooler nights when traveling from Mystic in November since evenings lows in Woodstock dip to °F. Finish your sightseeing early on the 9th (Mon) so you can travel to Simsbury.

Things to do in Woodstock

Parks Outdoors Trails

Side Trips

South Windsor, Manchester, Willimantic, Ellington, Coventry
Highlights from your plan
James L. Goodwin State Forest ©
James L. Goodwin State Forest
Taylor Brooke Winery ©
Taylor Brooke Winery
Woodstock Orchard ©
Woodstock Orchard

11
nights
Simsbury

Simsbury ©
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 °F, while at night they dip to °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

Side Trips

West Hartford, Farmington, Bloomfield, Granby, Connecticut
Highlights from your plan
Elizabeth Park ©
Elizabeth Park
Heublein Tower ©
Heublein Tower
Hill-Stead Museum ©
Hill-Stead Museum

11
nights
Washington

Washington ©
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 Reservation, 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 °F in December, and nighttime lows around °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

Side Trips

Litchfield, New Milford, Brookfield, Winsted, Ridgefield
Highlights from your plan
Kent Falls State Park ©
Kent Falls State Park
Gunn Historical Museum ©
Gunn Historical Museum
Hollister House Garden ©
Hollister House Garden

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