60 days in Connecticut Itinerary

60 days in Connecticut Itinerary

Created using Inspirock Connecticut vacation maker

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Route & dates

60 days in Connecticut Itinerary

Start: New York City
Drive:  1​h 30​min
1
Milford
— 20 nights
Drive:  1​h 15​min
2
Mystic
— 20 nights
Drive:  1​h 15​min
3
Manchester
— 19 nights
Drive:  2​h 45​min
End: New York City

20
nights
Milford

Milford ©
Milford is a Coterminous municipality within Coastal Connecticut and New Haven County, Connecticut, between Bridgeport, Connecticut and New Haven, Connecticut. Satisfy your inner culture vulture at Weir Farm National Historic Site and Yale University Art Gallery. Get some historical perspective at Sheffield Island Lighthouse and First Presbyterian Church. Explore Milford's surroundings by going to Wallingford (Gouveia Vineyards & Paradise Hills Vineyard), Norwalk River Valley Trail (in Wilton) and Thimble Islands (in Branford). Next up on the itinerary: admire the majestic nature at Silver Sands State Park, take in the dramatic scenery at Kent Falls State Park, tour the pleasant surroundings at Gulf Beach, and kick back and relax at Sasko Beach.

For ratings, traveler tips, more things to do, and tourist information, you can read our Milford trip builder app .

New York City to Milford is an approximately 1.5-hour car ride. In June, daytime highs in Milford are 78°F, while nighttime lows are 62°F. Wrap up your sightseeing on the 1st (Mon) early enough to drive to Mystic.

Things to do in Milford

Parks Outdoors Nature

Side Trips

New Haven, Stratford, Washington, Fairfield, Madison
Highlights from your plan
Hammonasset Beach State Park ©
Hammonasset Beach State Park
Yale University Art Gallery ©
Yale University Art Gallery
Weir Farm National Historic Site ©
Weir Farm National Historic Site

20
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Get in touch with nature at Fort Trumbull State Park and Dubois Beach. Olde Mistick Village and Jonathan Edwards Winery are good opportunities to explore the local culture. Venture out of the city with trips to Essex (Pratt House, Main Street Park, Essex Village, & more), Harvey's Beach (in Old Saybrook) and East Haddam (Fox Hopyard Golf Club & Devil's Hopyard State Park). Spend the 16th (Tue) exploring nature at Stewart B. McKinney National Wildlife Refuge. The adventure continues: see the interesting displays at Mystic Seaport Museum, go for a walk through Mystic River Historical Society, head outdoors with Sculpture Grounds, and try to win big at Foxwoods Resort Casino.

To find where to stay, photos, other places to visit, and more tourist information, read our Mystic online trip builder .

Getting from Milford to Mystic by car takes about 1.5 hours. Expect a daytime high around 80°F in July, and nighttime lows around 66°F. Finish your sightseeing early on the 21st (Sun) so you can drive to Manchester.

Things to do in Mystic

Parks Outdoors Historic Sites

Side Trips

Groton, New London, Stonington, Waterford, Mashantucket
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum
Foxwoods Resort Casino ©
Foxwoods Resort Casino
Olde Mistick Village ©
Olde Mistick Village

19
nights
Manchester

Manchester ©
Manchester is a town in Hartford County, Connecticut, United States. Get in touch with nature at Gillette Castle State Park and Vernon Rails-to-Trails. The Mark Twain House & Museum and Ancient Burying Ground will appeal to history buffs. Explore the numerous day-trip ideas around Manchester: Woodstock (Woodstock Orchard, Roseland Cottage, & more), Machimoodus State Park (in Moodus) and A Place Called Hope (in Killingworth). And it doesn't end there: hike along The Lodge at Crandall Park, explore the landscape on two wheels at Farmington Canal Heritage Trail, take a peaceful walk through American Legion and Peoples State Forests, and admire the majestic nature at Wadsworth Falls State Park.

To see photos, traveler tips, ratings, and more tourist information, read our Manchester road trip site .

Getting from Mystic to Manchester by car takes about 1.5 hours. July in Manchester sees daily highs of 85°F and lows of 67°F at night. Finish up your sightseeing early on the 9th (Fri) so you can travel back home.

Things to do in Manchester

Parks Outdoors Trails

Side Trips

Hartford, West Hartford, Litchfield, Winsted, Woodstock
Highlights from your plan
Gillette Castle State Park ©
Gillette Castle State Park
The Mark Twain House & Museum ©
The Mark Twain House & Museum
New Britain Museum of American Art ©

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