30 days in Connecticut Itinerary

30 days in Connecticut Itinerary

Created using Inspirock Connecticut attractions planner

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Make it your trip
Fly
1
Hartford
— 2 nights
Drive
2
Chaplin
— 2 nights
Drive
3
Chester
— 2 nights
Drive
4
Essex
— 2 nights
Drive
5
Mystic
— 2 nights
Drive
6
Guilford
— 2 nights
Drive
7
Madison
— 2 nights
Drive
8
Monroe
— 2 nights
Drive
9
Norwalk
— 2 nights
Drive
10
Ridgefield
— 2 nights
Drive
11
New Milford
— 2 nights
Drive
12
Washington
— 2 nights
Drive
13
Cornwall
— 2 nights
Drive
14
Kent
— 2 nights
Drive
15
Hartford
— 1 night
Fly

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Hartford

— 2 nights
Hartford is the capital of the U.S. state of Connecticut. Start off your visit on the 1st (Wed): find something for the whole family at Six Flags New England and then admire the masterpieces at Wadsworth Atheneum Museum of Art. Here are some ideas for day two: stroll through Elizabeth Park, then take an in-depth tour of The Mark Twain House & Museum, and then take in nature's colorful creations at Harriet Beecher Stowe Center.

To see ratings, reviews, photos, and more tourist information, you can read our Hartford trip app.

Miami to Hartford is an approximately 5-hour flight. You can also drive; or take a bus. Prepare for slightly colder weather when traveling from Miami in June: high temperatures in Hartford hover around 80°F and lows are around 60°F. Finish up your sightseeing early on the 3rd (Fri) so you can travel to Chaplin.

Things to do in Hartford

Museums · Parks · Historic Sites · Theme Parks

Side Trips

Chaplin

— 2 nights
Chaplin is a town in Windham County, Connecticut, United States. Kick off your visit on the 3rd (Fri): stroll around Breezy Picnic Grounds & Waterslides, then steep yourself in history at Roseland Cottage, and then do a tasting at Taylor Brooke Winery. On the 4th (Sat), you'll have a packed day of sightseeing: hike along Diana's Pool and then make a trip to Nathan Hale Homestead.

To find where to stay, reviews, maps, and other tourist information, read Chaplin travel itinerary planner.

Traveling by car from Hartford to Chaplin takes an hour. In June in Chaplin, expect temperatures between 79°F during the day and 57°F at night. Finish your sightseeing early on the 5th (Sun) so you can travel to Chester.

Things to do in Chaplin

Parks · Trails · Outdoors · Historic Sites

Side Trips

Chester

— 2 nights
Chester is a town in Middlesex County, Connecticut, United States. Start off your visit on the 5th (Sun): experience rural life at Lavender Pond Farm and then stroll through A Place Called Hope. On the 6th (Mon), you'll have a packed day of sightseeing: admire the majestic nature at Millers Pond State Park and then look for gifts at Lyman Orchards.

For where to stay, maps, more things to do, and tourist information, read our Chester trip planner.

Traveling by car from Chaplin to Chester takes 1.5 hours. In June, plan for daily highs up to 75°F, and evening lows to 58°F. You'll set off for Essex on the 7th (Tue).

Things to do in Chester

Parks · Nature · Wildlife · Shopping

Side Trips

Essex

— 2 nights
Essex is a town in Middlesex County, Connecticut, United States. Start off your visit on the 7th (Tue): see the interesting displays at Connecticut River Museum and then make a trip to Main Street Park, Essex Village. On the 8th (Wed), you'll have a packed day of sightseeing: immerse yourself in nature at Rocky Neck State Park and then admire the masterpieces at Florence Griswold Museum.

To see photos, where to stay, maps, and tourist information, use the Essex trip maker site.

Essex is just a stone's throw from Chester. In June, daily temperatures in Essex can reach 75°F, while at night they dip to 58°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive to Mystic.

Things to do in Essex

Museums · Nature · Parks · Shopping

Side Trips

Mystic

— 2 nights
A historical leading seaport, Mystic has maintained a strong respect for the past.
Start off your visit on the 9th (Thu): get engrossed in the history at Mystic Seaport Museum, see the interesting displays at The Submarine Force Museum, and then browse the exhibits of The Custom House Maritime Museum. On the 10th (Fri), you'll have a packed day of sightseeing: take an in-depth tour of Slater Memorial Museum, try to win big at Foxwoods Resort Casino, and then admire nature's wide array of creatures at Mystic Aquarium.

To see traveler tips, where to stay, ratings, and tourist information, read Mystic tour itinerary builder.

Mystic is very close to Essex. Expect a daytime high around 74°F in June, and nighttime lows around 58°F. Wrap up your sightseeing on the 11th (Sat) to allow time to drive to Guilford.

Things to do in Mystic

Museums · Tours · Outdoors · Fun & Games

Side Trips

Guilford

— 2 nights
Guilford is a town in New Haven County, Connecticut, United States, that borders Madison, Branford, North Branford and Durham, and is situated on I-95 and the coast. Kick off your visit on the 11th (Sat): step off the mainland to explore Thimble Islands and then relax in the rural setting at Bishop's Orchards. On the 12th (Sun), you'll have a packed day of sightseeing: get a new perspective on things with Boat Tours & Water Sports and then learn about winemaking at Gouveia Vineyards.

To see more things to do, other places to visit, maps, and other tourist information, use the Guilford journey planning app.

Traveling by car from Mystic to Guilford takes an hour. In June, daytime highs in Guilford are 75°F, while nighttime lows are 58°F. Cap off your sightseeing on the 13th (Mon) early enough to travel to Madison.

Things to do in Guilford

Nature · Tours · Outdoors · Parks

Side Trips

Madison

— 2 nights
Madison is a town in the southeastern corner of New Haven County, Connecticut, United States, occupying a central location on Connecticut's Long Island Sound shoreline. On the 13th (Mon), enjoy the sand and surf at Hammonasset Beach State Park and then look for gifts at RJ Julia Booksellers. Here are some ideas for day two: tour the pleasant surroundings at Meigs Point Nature Center and then revel in the low prices at Clinton Crossing Premium Outlets.

To find other places to visit, reviews, where to stay, and more tourist information, use the Madison trip itinerary builder website.

Madison is very close to Guilford. Expect a daytime high around 75°F in June, and nighttime lows around 58°F. You will leave for Monroe on the 15th (Wed).

Things to do in Madison

Parks · Shopping · Nature · Beaches

Side Trip

Monroe

— 2 nights
Monroe is a town in Fairfield County, Connecticut, United States. On the 15th (Wed), admire the majestic nature at Southford Falls State Park and then contemplate the waterfront views at Lake Zoar. Get ready for a full day of sightseeing on the next day: admire the majestic nature at Collis P. Huntington State Park and then sample the tasty concoctions at Veracious Brewing Company.

To see reviews, where to stay, maps, and tourist information, you can read our Monroe online travel planner.

You can drive from Madison to Monroe in an hour. In June, daily temperatures in Monroe can reach 75°F, while at night they dip to 57°F. Finish up your sightseeing early on the 17th (Fri) so you can travel to Norwalk.

Things to do in Monroe

Nature · Parks · Breweries & Distilleries

Side Trips

Norwalk

— 2 nights
Norwalk, is the sixth most populous city in the U.S. state of Connecticut. Kick off your visit on the 17th (Fri): learn about wildlife with up-close encounters at Beardsley Zoo, then explore the galleries of Lockwood-Mathews Mansion Museum, and then visit a coastal fixture at Sheffield Island Lighthouse. Here are some ideas for day two: explore the engaging exhibits at Stepping Stones Museum for Children, meet the residents at The Maritime Aquarium, and then soothe aching muscles at Work It Dance and Fitness.

To see maps, photos, reviews, and more tourist information, read our Norwalk road trip planning tool.

Drive from Monroe to Norwalk in an hour. June in Norwalk sees daily highs of 78°F and lows of 62°F at night. Wrap up your sightseeing on the 19th (Sun) early enough to drive to Ridgefield.

Things to do in Norwalk

Parks · Zoos & Aquariums · Museums · Historic Sites

Side Trip

Ridgefield

— 2 nights
Ridgefield is a town in Fairfield County, Connecticut, United States. On the 19th (Sun), explore the activities along Garden of Ideas, explore the world behind art at The Aldrich Contemporary Art Museum, and then tour the pleasant surroundings at Wolf Conservation Center. On the next day, admire the majestic nature at Harriman State Park, admire the striking features of Manitoga / The Russel Wright Design Center, and then experience rural life at Faraway Farm Alpacas.

Plan a Ridgefield trip in moments using our itinerary builder.

Ridgefield is just a stone's throw from Norwalk. Expect little chillier evenings in Ridgefield when traveling from Norwalk in June, with lows around 57°F. Finish up your sightseeing early on the 21st (Tue) so you can travel to New Milford.

Things to do in Ridgefield

Parks · Nature · Wildlife · Museums

Side Trips

New Milford

— 2 nights
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 21st (Tue): contemplate the waterfront views at Lovers Leap State Park and then stroll around Harrybrooke Park. On the 22nd (Wed), you'll have a packed day of sightseeing: immerse yourself in nature at Squantz Pond State Park and then learn about winemaking at DiGrazia Winery.

To see maps, more things to do, traveler tips, and more tourist information, go to the New Milford itinerary planner.

You can drive from Ridgefield to New Milford in an hour. In June in New Milford, expect temperatures between 77°F during the day and 57°F at night. Wrap up your sightseeing on the 23rd (Thu) to allow time to travel to Washington.

Things to do in New Milford

Parks · Nature · Trails · Outdoors

Side Trips

Washington

— 2 nights
Washington is a rural town in Litchfield County, Connecticut, in the New England region of the United States. On the 23rd (Thu), tour the pleasant surroundings at White Memorial Conservation Center and then learn about winemaking at Haight-Brown Vineyard. Keep things going the next day: see the interesting displays at Institute for American Indian Studies and then visit Hopkins Vineyard.

To see reviews, where to stay, photos, and other tourist information, read Washington road trip website.

Washington is very close to New Milford. In June in Washington, expect temperatures between 75°F during the day and 57°F at night. Finish up your sightseeing early on the 25th (Sat) so you can travel to Cornwall.

Things to do in Washington

Wineries · Museums · Wildlife · Neighborhoods

Side Trips

Cornwall

— 2 nights
Cornwall is a town in Litchfield County, Connecticut, United States. Kick off your visit on the 25th (Sat): tour the pleasant surroundings at Action Wildlife Foundation, then learn about winemaking at Sunset Meadow Vineyards, then look for gifts at Thorncrest Farm and Milk House Chocolate, and finally immerse yourself in nature at Haystack Mountain State Park. Get ready for a full day of sightseeing on the 26th (Sun): take in the views from West Cornwall Covered Bridge and then grab your bike and head to Harlem Valley Rail Trail.

To find maps and tourist information, go to the Cornwall trip itinerary planner.

Cornwall is just a stone's throw from Washington. In June, daytime highs in Cornwall are 75°F, while nighttime lows are 57°F. Finish up your sightseeing early on the 27th (Mon) so you can travel to Kent.

Things to do in Cornwall

Parks · Nature · Trails · Outdoors

Side Trips

Kent

— 2 nights
Kent is a town in Litchfield County, Connecticut, alongside the border with New York. On the 27th (Mon), snap pictures at Bull's Bridge and then admire the sheer force of Kent Falls State Park. Here are some ideas for day two: stroll around Macedonia Brook State Park and then do a tasting at Millbrook Vineyards & Winery.

To see more things to do, other places to visit, and more tourist information, read our Kent tour itinerary planner.

Kent is very close to Cornwall. In June, plan for daily highs up to 80°F, and evening lows to 57°F. Wrap up your sightseeing on the 29th (Wed) early enough to drive to Hartford.

Things to do in Kent

Nature · Parks · Wineries

Side Trip

Hartford

— 1 night
On the 29th (Wed), get a new perspective on nature at Dinosaur State Park, then cool off at Lake Compounce, and then ponder the world of politics at Connecticut State Capitol. Get ready for a full day of sightseeing on the 30th (Thu): walk around Stanley park.

To find ratings, more things to do, traveler tips, and other tourist information, you can read our Hartford travel planning tool.

Traveling by car from Kent to Hartford takes 1.5 hours. Wrap up your sightseeing by early afternoon on the 30th (Thu) to allow enough time to fly back home.

Things to do in Hartford

Theme Parks · Parks · 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.