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

Plan created by another user. Make it yours

Route & dates

New Milford
— 15 nights
— 17 nights

New Milford

New Milford ©
New Milford is a town in southern Litchfield County, Connecticut, United States, 14mi north of Danbury, on the Housatonic River. Get out of town with these interesting New Milford side-trips: Ridgefield (Garden of Ideas, ACT of Connecticut, &more). There's much more to do: explore the activities along Lovers Leap State Park, stroll around Harrybrooke Park, see the interesting displays at Danbury Railway Museum, and take a peaceful walk through Gurski Farm- Williams Park.

For maps, traveler tips, reviews, and tourist information, refer to the New Milford route planner.

Newark to New Milford is an approximately 2-hour car ride. Plan for a bit cooler temperatures traveling from Newark in November, with highs in New Milford at 51°F and lows at 31°F. On the 11th (Wed), you're off to Stratford.

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 the numerous day-trip ideas around Stratford: New Canaan (New Canaan Nature Center, St. Marks Episcopal Church, &more), Wilton (Norwalk River Valley Trail, Weir Farm National Historic Site, &more) and Norwalk (Sheffield Island Lighthouse, Center for Contemporary Printmaking, &more). Next up on the itinerary: indulge your thirst for a good beer at Two Roads Brewing Company, tour the pleasant surroundings at Short Beach, pick up a one of a kind souvenir at Stratford Antique Center, and take a peaceful walk through Roosevelt Forest.

For where to stay, more things to do, and more tourist information, read Stratford trip builder.

Drive from New Milford to Stratford in an hour. In December, daytime highs in Stratford are 45°F, while nighttime lows are 32°F. Wrap up your sightseeing on the 28th (Sat) to allow time to travel back home.

Things to do in Stratford

Parks · Museums · Historic Sites

Side Trips

Bridgeport, Stamford, Norwalk, Greenwich, Shelton
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