8 days in Connecticut Itinerary

8 days in Connecticut Itinerary

Created using Inspirock Connecticut tour builder

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Make it your trip
Fly to New York JFK, Train to New Haven
1
New Haven
— 1 night
Drive
2
Mystic
— 4 nights
Drive
3
Simsbury
— 2 nights
Drive to La Guardia Airport, Fly to Buffalo Niagara International Airport

S M T W T F S
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New Haven

— 1 night
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. Start off your visit on the 10th (Sat): admire the majestic nature at Sleeping Giant State Park, test your problem-solving skills at Adventure Rooms, and then stop by Lyman Orchards. On the next day, snap pictures at Pearl Harbor Memorial Bridge, explore the world behind art at Yale University Art Gallery, then admire the masterpieces at Yale Center for British Art, and finally gain insight at Yale University.

To see ratings, other places to visit, reviews, and tourist information, use the New Haven holiday planner.

Buffalo to New Haven is an approximately 6-hour combination of flight and train. You can also do a combination of flight and train; or drive; or do a combination of taxi and train. In October in New Haven, expect temperatures between 66°F during the day and 48°F at night. Wrap up your sightseeing on the 11th (Sun) early enough to drive to Mystic.

Things to do in New Haven

Museums · Nature · Parks · Shopping

Side Trips

Mystic

— 4 nights
A historical leading seaport, Mystic has maintained a strong respect for the past.
Venture out of the city with trips to Skydive Danielson (in Killingly), Roseland Cottage (in Woodstock) and Gillette Castle State Park (in East Haddam). And it doesn't end there: see the sky in a new way at Mystic Seaport Museum, step aboard Charles W. Morgan, contemplate the long history of Olde Mistick Village, and stop by The Spice & Tea Exchange.

To find other places to visit, ratings, more things to do, and more tourist information, you can read our Mystic trip planning website.

Traveling by car from New Haven to Mystic takes an hour. Alternatively, you can drive; or take a train. In October in Mystic, expect temperatures between 65°F during the day and 48°F at night. Cap off your sightseeing on the 15th (Thu) early enough to go by car to Simsbury.

Things to do in Mystic

Tours · Outdoors · Historic Sites · Museums

Side Trips

Simsbury

— 2 nights
Simsbury is an affluent town in Hartford County, Connecticut, United States. On the 16th (Fri), explore the world behind art at Hill-Stead Museum, make a trip to Heublein Tower, then tour the pleasant surroundings at Talcott Mountain State Park, and finally snap pictures at Old Drake Hill Flower Bridge. Get ready for a full day of sightseeing on the next day: learn about winemaking at Sunset Meadow Vineyards, admire the majestic nature at Kent Falls State Park, and then test your problem-solving skills at Complexity: A Puzzling Adventure.

To find ratings, traveler tips, more things to do, and tourist information, read Simsbury online trip planner.

You can drive from Mystic to Simsbury in 1.5 hours. Alternatively, you can drive. Expect a daytime high around 66°F in October, and nighttime lows around 44°F. Finish up your sightseeing early on the 17th (Sat) so you can travel back home.

Things to do in Simsbury

Parks · Nature · Trails · Outdoors

Side Trips

Connecticut travel guide

4.3
Historic Sites · Aquariums · Theaters
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.