30 days in Connecticut Itinerary

30 days in Connecticut Itinerary

Created using Inspirock Connecticut visit 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 18th (Wed): get in on the family fun at Six Flags New England and then admire the masterpieces at Wadsworth Atheneum Museum of Art. Get ready for a full day of sightseeing on the next day: take in nature's colorful creations at Elizabeth Park, then browse the exhibits of The Mark Twain House & Museum, and then take in nature's colorful creations at Harriet Beecher Stowe Center.

For other places to visit and more tourist information, go to the Hartford trip itinerary planner.

Miami to Hartford is an approximately 5-hour flight. You can also drive; or take a bus. Prepare for little chillier weather when traveling from Miami in August: high temperatures in Hartford hover around 83°F and lows are around 64°F. Wrap up your sightseeing on the 20th (Fri) early enough to travel to Chaplin.
Museums · Historic Sites · Parks · Outdoors
Side Trips

Chaplin — 2 nights

Chaplin is a town in Windham County, Connecticut, United States. Start off your visit on the 20th (Fri): walk around Breezy Picnic Grounds & Waterslides, steep yourself in history at Roseland Cottage, and then learn about winemaking at Taylor Brooke Winery. Get ready for a full day of sightseeing on the next day: hike along Diana's Pool and then don't miss a visit to Nathan Hale Homestead.

For photos, reviews, and more tourist information, read our Chaplin trip planner.

Traveling by car from Hartford to Chaplin takes an hour. August in Chaplin sees daily highs of 82°F and lows of 61°F at night. Cap off your sightseeing on the 22nd (Sun) early enough to travel to Chester.
Parks · Outdoors · Trails · Historic Sites
Side Trips

Chester — 2 nights

Chester is a town in Middlesex County, Connecticut, United States. Start off your visit on the 22nd (Sun): relax in the rural setting at Lavender Pond Farm and then stroll through A Place Called Hope. On the next day, immerse yourself in nature at Millers Pond State Park and then relax in the rural setting at Lyman Orchards.

Before you visit Chester, use our trip planner to discover what you can do and see there.

Getting from Chaplin to Chester by car takes about 1.5 hours. In August, daily temperatures in Chester can reach 79°F, while at night they dip to 63°F. You'll set off for Essex on the 24th (Tue).
Parks · Wildlife · Shopping · Nature
Side Trips

Essex — 2 nights

Essex is a town in Middlesex County, Connecticut, United States. Start off your visit on the 24th (Tue): take in the waterfront at Connecticut River Museum and then make a trip to Main Street Park, Essex Village. Keep things going the next day: immerse yourself in nature at Rocky Neck State Park and then admire the masterpieces at Florence Griswold Museum.

To find photos, maps, where to stay, and other tourist information, read Essex trip itinerary planning website.

Essex is just a short distance from Chester. In August in Essex, expect temperatures between 79°F during the day and 63°F at night. Wrap up your sightseeing on the 26th (Thu) early enough to drive to Mystic.
Shopping · Museums · Outdoors · Historic Sites
Side Trips

Mystic — 2 nights

A historical leading seaport, Mystic has maintained a strong respect for the past.
Kick off your visit on the 26th (Thu): shop like a local with Mystic Seaport Museum, then examine the collection at The Submarine Force Museum, and then browse the exhibits of The Custom House Maritime Museum. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Slater Memorial Museum, try your luck at Foxwoods Resort Casino, and then get up close and personal with brilliant marine life at Mystic Aquarium.

To see where to stay, other places to visit, more things to do, and other tourist information, read Mystic road trip planning app.

Mystic is just a stone's throw from Essex. Expect a daytime high around 79°F in August, and nighttime lows around 63°F. Finish your sightseeing early on the 28th (Sat) so you can drive to Guilford.
Museums · Outdoors · Shopping · 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. Start off your visit on the 28th (Sat): head off the coast to Thimble Islands and then relax in the rural setting at Bishop's Orchards. Keep things going the next day: get a new perspective on things with Boat Tours & Water Sports and then learn about winemaking at Gouveia Vineyards.

To see photos, more things to do, and more tourist information, read our Guilford online trip itinerary maker.

Traveling by car from Mystic to Guilford takes an hour. In August, plan for daily highs up to 79°F, and evening lows to 63°F. Cap off your sightseeing on the 30th (Mon) early enough to travel to Madison.
Outdoors · Nature · Tours · 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. Start off your visit on the 30th (Mon): enjoy the sand and surf at Hammonasset Beach State Park and then stop by RJ Julia Booksellers. Here are some ideas for day two: stroll through Meigs Point Nature Center and then browse the different shops at Clinton Crossing Premium Outlets.

For photos, where to stay, maps, and more tourist information, read our Madison visit planner.

Madison is very close to Guilford. August in Madison sees daily highs of 79°F and lows of 63°F at night. On the 1st (Wed), you're off to Monroe.
Shopping · Parks · Beaches · Outdoors
Side Trip

Monroe — 2 nights

Monroe is a town in Fairfield County, Connecticut, United States. Start off your visit on the 1st (Wed): immerse yourself in nature at Southford Falls State Park and then explore the activities along Lake Zoar. Here are some ideas for day two: immerse yourself in nature at Collis P. Huntington State Park and then indulge your thirst for a good beer at Veracious Brewing Company.

For more things to do, other places to visit, reviews, and other tourist information, refer to the Monroe travel route planner.

Drive from Madison to Monroe in an hour. September in Monroe sees daily highs of 74°F and lows of 54°F at night. Cap off your sightseeing on the 3rd (Fri) early enough to travel to Norwalk.
Nature · Parks · Breweries & Distilleries
Side Trips

Norwalk — 2 nights

Norwalk, is the sixth most populous city in the U.S. state of Connecticut. On the 3rd (Fri), get to know the resident critters at Beardsley Zoo, take an in-depth tour of Lockwood-Mathews Mansion Museum, and then enjoy the sea views from Sheffield Island Lighthouse. On your second day here, explore the engaging exhibits at Stepping Stones Museum for Children, then meet the residents at The Maritime Aquarium, and then relax and rejuvenate at Work It Dance and Fitness.

To see maps, where to stay, other places to visit, and other tourist information, read our Norwalk trip itinerary site.

You can drive from Monroe to Norwalk in an hour. Expect a bit warmer evenings in Norwalk when traveling from Monroe in September, with lows around 61°F. Finish your sightseeing early on the 5th (Sun) so you can drive to Ridgefield.
Zoos & Aquariums · Parks · Historic Sites · Museums
Side Trip

Ridgefield — 2 nights

Ridgefield is a town in Fairfield County, Connecticut, United States. On the 5th (Sun), contemplate the waterfront views at Garden of Ideas, then explore the world behind art at The Aldrich Contemporary Art Museum, and then stroll through Wolf Conservation Center. Get ready for a full day of sightseeing on the next day: immerse yourself in nature at Harriman State Park, steep yourself in history at Manitoga / The Russel Wright Design Center, and then relax in the rural setting at Faraway Farm Alpacas.

For photos, where to stay, more things to do, and more tourist information, refer to the Ridgefield trip itinerary maker site.

Ridgefield is very close to Norwalk. Traveling from Norwalk in September, expect a bit cooler with lows of 54°F in Ridgefield. Finish up your sightseeing early on the 7th (Tue) so you can travel to New Milford.
Parks · Nature · Wildlife · Historic Sites
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. Kick off your visit on the 7th (Tue): stroll through Lovers Leap State Park and then tour the pleasant surroundings at Harrybrooke Park. On the 8th (Wed), you'll have a packed day of sightseeing: admire the majestic nature at Squantz Pond State Park and then do a tasting at DiGrazia Winery.

For ratings, other places to visit, reviews, and other tourist information, read New Milford trip planning site.

Getting from Ridgefield to New Milford by car takes about an hour. In September, plan for daily highs up to 76°F, and evening lows to 54°F. Cap off your sightseeing on the 9th (Thu) early enough to travel to Washington.
Parks · Nature · Outdoors · Wildlife
Side Trips

Washington — 2 nights

Washington is a rural town in Litchfield County, Connecticut, in the New England region of the United States. Kick off your visit on the 9th (Thu): tour the pleasant surroundings at White Memorial Conservation Center and then do a tasting at Haight-Brown Vineyard. Keep things going the next day: see the interesting displays at Institute for American Indian Studies and then wander the streets of Hopkins Vineyard.

To find ratings, reviews, other places to visit, and tourist information, you can read our Washington itinerary builder app.

Washington is just a stone's throw from New Milford. In September in Washington, expect temperatures between 74°F during the day and 54°F at night. Wrap up your sightseeing on the 11th (Sat) to allow time to travel to Cornwall.
Wineries · Wildlife · Neighborhoods · Museums
Side Trips

Cornwall — 2 nights

Cornwall is a town in Litchfield County, Connecticut, United States. On the 11th (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 admire the majestic nature at Haystack Mountain State Park. On your second day here, snap pictures at West Cornwall Covered Bridge and then grab your bike and head to Harlem Valley Rail Trail.

For traveler tips, more things to do, where to stay, and other tourist information, you can read our Cornwall trip planner.

Cornwall is very close to Washington. In September, daily temperatures in Cornwall can reach 74°F, while at night they dip to 54°F. Cap off your sightseeing on the 13th (Mon) early enough to travel to Kent.
Parks · Outdoors · Wildlife · Nature
Side Trips

Kent — 2 nights

Kent is a town in Litchfield County, Connecticut, alongside the border with New York. On the 13th (Mon), take in the views from Bull's Bridge and then admire the sheer force of Kent Falls State Park. On the next day, immerse yourself in nature at Macedonia Brook State Park and then learn about winemaking at Millbrook Vineyards & Winery.

To see reviews, where to stay, other places to visit, and tourist information, you can read our Kent itinerary planner.

Kent is just a stone's throw from Cornwall. Expect a daytime high around 78°F in September, and nighttime lows around 53°F. Finish your sightseeing early on the 15th (Wed) to allow enough time to drive to Hartford.
Nature · Parks · Wineries
Side Trip

Hartford — 1 night

On the 15th (Wed), examine the collection at Dinosaur State Park, then cool off at Lake Compounce, and then get a sense of history and politics at Connecticut State Capitol. On the 16th (Thu), you'll have a packed day of sightseeing: stroll around Stanley park.

For traveler tips, photos, reviews, and other tourist information, read Hartford online trip itinerary planner.

Getting from Kent to Hartford by car takes about 1.5 hours. Wrap up your sightseeing by early afternoon on the 16th (Thu) to allow enough time to fly back home.
Theme Parks · Parks · Museums
Side Trips

Connecticut travel guide

4.3
Aquariums · Room Escape Games · 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.