33 days in Connecticut's Fairfield County Itinerary

33 days in Connecticut's Fairfield County Itinerary

Created using Inspirock Connecticut's Fairfield County trip itinerary planner

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Route & dates

33 days in Connecticut's Fairfield County Itinerary

Start: Newark
Drive:  1​h 45​min
New Milford
— 15 nights
Drive:  1​h 15​min
— 17 nights
Drive:  1​h 45​min
End: Newark

New Milford

New Milford ©
New Milford is a town in southern Litchfield County, Connecticut, United States, 14mi north of Danbury, on the Housatonic River. Explore the numerous day-trip ideas around New Milford: Ridgefield (Garden of Ideas, ACT of Connecticut, & more). There's lots more to do: grab your bike and head to Sega Meadows Park, identify plant and animal life at Harrybrooke Park, browse the eclectic array of goods at Elephant's Trunk Flea Market, and get your game on at Monster Mini Golf and Laser Tag.

To find where to stay, maps, and more tourist information, read our New Milford journey planner.

Newark to New Milford is an approximately 2-hour car ride. Expect a bit cooler temperatures when traveling from Newark in November; daily highs in New Milford reach 51°F and lows reach 31°F. On the 11th (Wed), you're off toStratford.

Things to do in New Milford

Parks Museums Outdoors

Side Trips

Danbury, Brookfield, Ridgefield, Bethel
Highlights from your plan
Tarrywile Park & Mansion ©
Tarrywile Park & Mansion
Lovers Leap State Park ©
Lovers Leap State Park
Harrybrooke Park ©
Harrybrooke Park


Stratford ©
Stratford is a town in Fairfield County, Connecticut, United States. Explore Stratford's surroundings by going to New Canaan (New Canaan Nature Center, St. Marks Episcopal Church, & more), Norwalk (Sheffield Island Lighthouse, Center for Contemporary Printmaking, & more) and Wilton (Weir Farm National Historic Site & Soaring Adventures of America, Inc.). And it doesn't end there: sample the tasty concoctions at Two Roads Brewing Company, get engrossed in the history at Perry House, hike along Pequonnock River Trail, and browse for treasures at Stratford Antique Center.

For other places to visit, traveler tips, reviews, and other tourist information, you can read our Stratford trip itinerary maker .

Drive from New Milford to Stratford in an hour. In December in Stratford, expect temperatures between 45°F during the day and 32°F at night. Finish your sightseeing early on the 28th (Sat) so you can travel back home.

Things to do in Stratford

Parks Museums Historic Sites

Side Trips

Bridgeport, Stamford, Norwalk, Westport, New Canaan
Highlights from your plan
The Maritime Aquarium ©
The Maritime Aquarium
Two Roads Brewing Company ©
Two Roads Brewing Company
Boothe Memorial Park and Museum ©
Boothe Memorial Park and Museum