4 days in Connecticut Itinerary

4 days in Connecticut Itinerary

Created using Inspirock Connecticut travel route maker

©
This plan was created by another user.  Make it your plan

Route & dates

4 days in Connecticut Itinerary

Start: Boston
train:  1​h 45​min
1
Mystic
— 1 night
Drive:  2​h
2
New Milford
— 2 nights
Drive:  2​h 45​min
End: Boston

1
night
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Kick off your visit on the 24th (Thu): look for gifts at The Book Barn, then browse the fresh offerings at Stonington Village Farmers' Market, and then try to win big at Foxwoods Resort Casino. On the 25th (Fri), you'll have a packed day of sightseeing: take a tour of Charles W. Morgan, see the interesting displays at Mystic Seaport Museum, and then do a tasting at Taylor Brooke Winery.

To find ratings, more things to do, reviews, and more tourist information, use the Mystic planner .

Boston to Mystic is an approximately 2-hour train ride. You can also drive. October in Mystic sees daily highs of 65°F and lows of 48°F at night. Finish up your sightseeing early on the 25th (Fri) so you can travel to New Milford.

Things to do in Mystic

Museums Casinos Fun & Games

Side Trips

Taylor Brooke Winery, The Book Barn, Stonington Village Farmers' Market, Foxwoods Resort Casino
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum
The Book Barn ©
The Book Barn
Foxwoods Resort Casino ©
Foxwoods Resort Casino

2
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. Start off your visit on the 26th (Sat): do a tasting at Walker Road Vineyards, do a tasting at Jones Family Farm, then look for gifts at Lyman Orchards, and finally indulge your thirst for a good beer at Thimble Islands Brewing Company. Here are some ideas for day two: browse the eclectic array of goods at Elephant's Trunk Flea Market, experience rural life at White Silo Farm & Winery, then do a tasting at Sunset Meadow Vineyards, and finally take in nature's colorful creations at Hollister House Garden.

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

Traveling by car from Mystic to New Milford takes 2 hours. In October in New Milford, expect temperatures between 65°F during the day and 44°F at night. Cap off your sightseeing on the 27th (Sun) early enough to travel back home.

Things to do in New Milford

Wineries Shopping Breweries & Distilleries

Side Trips

Thimble Islands Brewing Company, Sunset Meadow Vineyards, Walker Road Vineyards, Hollister House Garden, Jones Family Farm
Highlights from your plan
Elephant's Trunk Flea Market ©
Elephant's Trunk Flea Market
Lyman Orchards ©
Lyman Orchards
White Silo Farm & Winery ©
White Silo Farm & Winery

Similar Plans

7 days in Connecticut BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in New York City & Connecticut BY A USER FROM UNITED STATES April, culture, historic sites, museums, popular sights PREFERENCES: April, culture, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Connecticut BY A USER FROM UNITED STATES August, teens, outdoors, historic sites, museums, wildlife, popular sights PREFERENCES: August, teens, outdoors, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Connecticut BY A USER FROM UNITED STATES April, teens, popular sights PREFERENCES: April, teens ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Connecticut BY A USER FROM UNITED STATES September, kids, fast-paced, popular sights PREFERENCES: September, kids ATTRACTION STYLE: Popular sights PACE: Fast-paced 5 days in Connecticut BY A USER FROM UNITED STATES August, teens, popular sights PREFERENCES: August, teens ATTRACTION STYLE: Popular sights PACE: Medium 6 days in United States BY A USER FROM UNITED STATES May, outdoors, relaxing, beaches, historic sites, museums, popular sights PREFERENCES: May, outdoors, relaxing, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Connecticut BY A USER FROM UNITED STATES August, culture, beaches, historic sites, wildlife, popular sights PREFERENCES: August, culture, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Connecticut BY A USER FROM SINGAPORE August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Connecticut BY A USER FROM UNITED STATES July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Connecticut, Philadelphia & Newark BY A USER FROM UNITED STATES August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Connecticut BY A USER FROM UNITED STATES August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium
View more plans