53 days in Connecticut Itinerary

53 days in Connecticut Itinerary

Created using Inspirock Connecticut trip planner

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Route & dates

53 days in Connecticut Itinerary

Start: Newark
Drive:  2​h
1
New Haven
— 10 nights
Drive:  1​h
2
Mystic
— 10 nights
Drive:  1​h 15​min
3
Woodstock
— 10 nights
Drive:  1​h 15​min
4
Simsbury
— 11 nights
Drive:  1​h 15​min
5
Washington
— 11 nights
Drive:  2​h 15​min
End: Newark

10
nights
New Haven

New Haven ©
New Haven, in the U.S. You'll find plenty of places to visit near New Haven: Panthorn Park (in Plantsville), New Britain Museum of American Art (in New Britain) and Still Hill Brewery (in Rocky Hill). There's lots more to do: explore the world behind art at Yale University Art Gallery, get lost in a book at Beinecke Rare Book & Manuscript Library, experience rural life at Gotta's Farm and Cider Mill, and trek along Pequonnock River Trail.

For more things to do, ratings, reviews, and more tourist information, go to the New Haven online holiday builder .

Newark to New Haven is an approximately 2-hour car ride. In November, daytime highs in New Haven are 53°F, while nighttime lows are 36°F. Wrap up your sightseeing on the 19th (Tue) early enough to drive to Mystic.

Things to do in New Haven

Parks Museums Historic Sites

Side Trips

Hartford, New Canaan, Stratford, Wilton, Stamford
Highlights from your plan
Yale University Art Gallery ©
Yale University Art Gallery
Beinecke Rare Book & Manuscript Library ©
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: Essex (Main Street Park, Essex Village & Essex Library Association), East Haddam (Ray of Light Farm, Gillette Castle State Park, & more) and DEEP Marine Headquarters - Ferry Landing Park (in Old Lyme). There's lots more to do: see the interesting displays at Mystic Seaport Museum, step aboard Charles W. Morgan, snap pictures at Mystic River Bascule Bridge, and observe the fascinating underwater world at Mystic Aquarium.

To see traveler tips, more things to do, maps, and tourist information, use the Mystic road trip app .

Drive from New Haven to Mystic in an hour. Alternatively, you can take a train; or take a bus. In November in Mystic, expect temperatures between 54°F during the day and 37°F at night. Finish your sightseeing early on the 29th (Fri) so you can drive to Woodstock.

Things to do in Mystic

Parks Museums Historic Sites

Side Trips

Groton, Waterford, Old Lyme, East Haddam, Mashantucket
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 Woodstock's surroundings by going to The Lodge at Crandall Park (in Tolland), Stafford Library (in Stafford) and Gay City State Park (in Hebron). There's lots more to do: steep yourself in history at Roseland Cottage, relax in the rural setting at Woodstock Orchard, hike along Vernon Rails-to-Trails, and head outdoors with Nomads Outdoor Adventure.

To find ratings, other places to visit, traveler tips, and more tourist information, you can read our Woodstock tour itinerary builder .

Drive from Mystic to Woodstock in 1.5 hours. Traveling from Mystic in November, expect little chillier with lows of 32°F in Woodstock. 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, Windsor Locks, Coventry, Ellington
Highlights from your plan
James L. Goodwin State Forest ©
James L. Goodwin State Forest
Roseland Cottage ©
Roseland Cottage
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, classes, nature, and historic sites. Your plan includes some of its best attractions: stroll through Talcott Mountain State Park, trek along West Hartford Reservoir, grab your bike and head to Farmington Canal Heritage Trail, and walk around Elizabeth Park.

To find traveler tips, reviews, photos, and tourist information, read our Simsbury online travel route builder .

Traveling by car from Woodstock to Simsbury takes 1.5 hours. December in Simsbury sees daily highs of 42°F and lows of 27°F at night. Wrap up your sightseeing on the 20th (Fri) to allow 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
Talcott Mountain State Park ©
Talcott Mountain State Park
Heublein Tower ©
Heublein Tower
Old Drake Hill Flower Bridge ©
Old Drake Hill Flower Bridge

11
nights
Washington

Washington ©
Washington is a rural town in Litchfield County, Connecticut, in the New England region of the United States. Venture out of the city with trips to Campbell Falls State Park (in Norfolk), Lime Rock Park (in Lakeville) and Beckley Furnace Industrial Monument (in East Canaan). There's lots more to do: look for all kinds of wild species at Steep Rock Reservation, browse the collection at Scoville Memorial Library, make a trip to ACT of Connecticut, and examine the collection at Institute for American Indian Studies.

To find maps, reviews, and other tourist information, you can read our Washington vacation builder app .

You can drive from Simsbury to Washington in 1.5 hours. In December, daytime highs in Washington are 41°F, while nighttime lows are 28°F. Wrap up your sightseeing by early afternoon on the 31st (Tue) to allow time for travel back home.

Things to do in Washington

Parks Museums Nature

Side Trips

Litchfield, New Milford, Winsted, Brookfield, Kent
Highlights from your plan
Kent Falls State Park ©
Kent Falls State Park
Gunn Historical Museum ©
Gunn Historical Museum
Institute for American Indian Studies ©

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