42 days in Connecticut Itinerary

42 days in Connecticut Itinerary

Created using Inspirock Connecticut planner

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Route & dates

42 days in Connecticut Itinerary

Start: Boston
Drive:  2​h 15​min
1
Manchester
— 12 nights
Drive:  1​h 15​min
2
Milford
— 14 nights
Drive:  1​h 15​min
3
Mystic
— 15 nights
train:  1​h 45​min
End: Boston

12
nights
Manchester

Manchester ©
Manchester is a town in Hartford County, Connecticut, United States. The Mark Twain House & Museum and New England Air Museum will appeal to museum buffs. Gillette Castle State Park and Webb Deane Stevens Museum will appeal to history buffs. Venture out of the city with trips to Litchfield (Litchfield First Congregational Church, Livingston Ripley Waterfowl Conservancy, & more), Granby (McLean Game Refuge & Enders Falls) and Winsted (Winchester Historical Society & Soldiers' Monument and Memorial Park). The adventure continues: take in the awesome beauty at Case Mountain, admire the majestic nature at Machimoodus State Park, stroll through Talcott Mountain State Park, and admire the masterpieces at New Britain Museum of American Art.

To see where to stay, more things to do, ratings, and tourist information, use the Manchester trip planner.

Boston to Manchester is an approximately 2-hour car ride. In May, daytime highs in Manchester are 72°F, while nighttime lows are 51°F. Cap off your sightseeing on the 31st (Fri) early enough to travel to Milford.

Things to do in Manchester

Parks Outdoors Nature

Side Trips

Hartford, Litchfield, Windsor Locks, Norfolk, Granby
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 ©

14
nights
Milford

Milford ©
Milford is a Coterminous municipality within Coastal Connecticut and New Haven County, Connecticut, between Bridgeport, Connecticut and New Haven, Connecticut. Get outdoors at Hammonasset Beach State Park and Walnut Beach. Satisfy your inner culture vulture at Yale University Art Gallery and Weir Farm National Historic Site. You'll find plenty of places to visit near Milford: Madison (The Shoreline Greenway Trail & Meigs Point Nature Center), Rosabianca Vineyards (in Northford) and Thimble Islands (in Branford). And it doesn't end there: immerse yourself in nature at Silver Sands State Park, identify plant and animal life at White Memorial Conservation Center, trek along New Canaan Nature Center, and tour the pleasant surroundings at Macricostas Preserve.

To see ratings, photos, more things to do, and other tourist information, go to the Milford road trip site .

Traveling by car from Manchester to Milford takes an hour. May in Milford sees daily highs of 69°F and lows of 52°F at night. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Mystic.

Things to do in Milford

Parks Outdoors Nature

Side Trips

New Haven, Stratford, Washington, Madison, Waterbury
Highlights from your plan
Hammonasset Beach State Park ©
Hammonasset Beach State Park
Yale University Art Gallery ©
Yale University Art Gallery

15
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Escape the urban bustle at Harkness Memorial State Park and Rocky Neck State Park. Let the collections at Mystic Seaport Museum and Florence Griswold Museum capture your imagination. Explore Mystic's surroundings by going to East Haddam (Devil's Hopyard State Park & Fox Hopyard Golf Club), Prudence Crandall Museum (in Canterbury) and Sculpture Grounds (in Old Lyme). The adventure continues: steep yourself in history at Olde Mistick Village, examine the collection at The Submarine Force Museum, shop like a local with Stonington Vineyards, and immerse yourself in nature at Fort Trumbull State Park.

To see more things to do, maps, where to stay, and other tourist information, refer to the Mystic driving holiday tool .

Traveling by car from Milford to Mystic takes 1.5 hours. In June in Mystic, expect temperatures between 74°F during the day and 58°F at night. Cap off your sightseeing on the 29th (Sat) early enough to catch the train back home.

Things to do in Mystic

Parks Outdoors Museums

Side Trips

Stonington, Groton, New London, Waterford, East Lyme
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum
Foxwoods Resort Casino ©
Foxwoods Resort Casino
The Submarine Force Museum ©
The Submarine Force Museum

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