15 days in Connecticut Itinerary

15 days in Connecticut Itinerary

Created using Inspirock Connecticut attractions planner

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Make it your trip
Drive
1
New Haven
— 2 nights
Drive
2
Mystic
— 4 nights
Drive
3
Woodstock
— 2 nights
Drive
4
Simsbury
— 3 nights
Drive
5
Kent
— 3 nights
Drive

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New Haven

— 2 nights
New Haven, in the U.S. state of Connecticut, is the principal municipality in Greater New Haven, which had a total population of 862,477 in 2010. Your day by day itinerary now includes St. Mary's Church, East Rock Park and Drazen Orchards. There's lots more to do: explore the world behind art at Yale Center for British Art, immerse yourself in nature at Sleeping Giant State Park, take an in-depth tour of Boothe Memorial Park and Museum, and learn about wildlife with up-close encounters at Beardsley Zoo.

For other places to visit, photos, ratings, and more tourist information, use the New Haven trip itinerary maker website.

Hartford to New Haven is an approximately 1-hour car ride. You can also take a train; or take a bus. In October, daily temperatures in New Haven can reach 66°F, while at night they dip to 48°F. Finish up your sightseeing early on the 12th (Tue) so you can go by car to Mystic.

Things to do in New Haven

Parks · Museums · Historic Sites · Nature

Side Trips

Mystic

— 4 nights
A historical leading seaport, Mystic has maintained a strong respect for the past.
You'll find plenty of places to visit near Mystic: Gillette Castle State Park (in East Haddam) and Slater Memorial Museum (in Norwich). The adventure continues: look and learn at Mystic Seaport Museum, see the interesting displays at The Submarine Force Museum, observe the fascinating underwater world at Mystic Aquarium, and snap pictures at Mystic River Bascule Bridge.

For more things to do, other places to visit, reviews, and more tourist information, read Mystic trip itinerary planner.

Traveling by car from New Haven to Mystic takes an hour. Alternatively, you can take a train. In October, daily temperatures in Mystic can reach 65°F, while at night they dip to 48°F. Finish your sightseeing early on the 16th (Sat) to allow enough time to drive to Woodstock.

Things to do in Mystic

Museums · Shopping · Parks · Historic Sites

Side Trips

Woodstock

— 2 nights
Woodstock is a town in Windham County, Connecticut, United States. Kick off your visit on the 17th (Sun): relax in the rural setting at Woodstock Orchard, contemplate the long history of Roseland Cottage, and then stroll through Airline North State Park Trail. Get ready for a full day of sightseeing on the next day: trek along Shenipsit Lake Trail - Blue Blazed, then trek along The Lodge at Crandall Park, and then do a tasting at Taylor Brooke Winery.

To see traveler tips, reviews, and tourist information, you can read our Woodstock online trip itinerary builder.

Traveling by car from Mystic to Woodstock takes 1.5 hours. In October, daytime highs in Woodstock are 66°F, while nighttime lows are 44°F. Cap off your sightseeing on the 18th (Mon) early enough to travel to Simsbury.

Things to do in Woodstock

Parks · Trails · Outdoors · Wildlife

Side Trips

Simsbury

— 3 nights
Simsbury is an affluent town in Hartford County, Connecticut, United States. When in Simsbury, make a side trip to see Rogers Orchards in Southington, approximately Southington away. There's much more to do: stroll through Talcott Mountain State Park, experience rural life at Westmoor Park, admire the masterpieces at Hill-Stead Museum, and hike along Farmington Valley Greenway.

To find other places to visit, ratings, where to stay, and more tourist information, go to the Simsbury road trip app.

Traveling by car from Woodstock to Simsbury takes 1.5 hours. In October, daytime highs in Simsbury are 66°F, while nighttime lows are 44°F. Wrap up your sightseeing on the 21st (Thu) to allow time to travel to Kent.

Things to do in Simsbury

Parks · Trails · Outdoors · Museums

Side Trips

Kent

— 3 nights
Kent is a town in Litchfield County, Connecticut, alongside the border with New York. You'll find plenty of places to visit near Kent: Millbrook Vineyards & Winery (in Millbrook) and Bash Bish Falls (in Mount Washington). There's still lots to do: admire the sheer force of Kent Falls State Park, look for gifts at Thorncrest Farm and Milk House Chocolate, do a tasting at Sunset Meadow Vineyards, and see the interesting displays at Connecticut Antique Machinery.

To find maps and other tourist information, read Kent trip maker.

You can drive from Simsbury to Kent in 1.5 hours. Expect a daytime high around 67°F in October, and nighttime lows around 43°F. Finish up your sightseeing early on the 24th (Sun) so you can go by car back home.

Things to do in Kent

Parks · Nature · Wineries · Museums

Side Trips

Connecticut travel guide

4.3
Aquariums · Theaters · Observatories
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.