22 days in Connecticut Itinerary

22 days in Connecticut Itinerary

Created using Inspirock Connecticut Trip Planner

©
Plan created by another user. Make it yours

Route & dates

1
Stamford
— 1 night
2
Norwalk
— 1 night
3
Redding
— 1 night
4
Danbury
— 1 night
5
Sherman
— 1 night
6
Milford
— 2 nights
7
New Haven
— 4 nights
8
Hartford
— 1 night
9
Haddam
— 1 night
10
Colchester
— 1 night
11
Niantic
— 1 night
12
Groton
— 2 nights
13
Mystic
— 3 nights
14
Branford
— 1 night

1
night
Stamford

Stamford ©
Stamford is a city in Fairfield County, Connecticut, United States. Kick off your visit on the 13th (Sun): contemplate the long history of Sagamore Hill National Historic Site and then immerse yourself in nature at Caumsett State Park.

To see photos, ratings, other places to visit, and tourist information, read Stamford road trip tool.

New York City to Stamford is an approximately 1.5-hour car ride. Plan for slightly colder nights when traveling from New York City in August since evenings lows in Stamford dip to 64°F. Wrap up your sightseeing on the 14th (Mon) to allow time to drive to Norwalk.

Things to do in Stamford

Nature · Parks · Museums

Side Trips

Caumsett State Park, Sagamore Hill National Historic Site
Highlights from your plan
Sagamore Hill National Historic Site ©
Sagamore Hill National Historic Site
Caumsett State Park ©
Caumsett State Park

1
night
Norwalk

Norwalk ©
Norwalk, is the sixth most populous city in the U.S. Kick off your visit on the 14th (Mon): enjoy the sea views from Sheffield Island Lighthouse and then take an in-depth tour of Fairfield Museum and History Center.

To see reviews, maps, ratings, and other tourist information, go to the Norwalk trip itinerary site.

Norwalk is very close to Stamford. In August, daily temperatures in Norwalk can reach 82°F, while at night they dip to 67°F. Cap off your sightseeing on the 15th (Tue) early enough to travel to Redding.

Things to do in Norwalk

Historic Sites · Museums

Side Trip

Fairfield Museum and History Center
Highlights from your plan
Sheffield Island Lighthouse ©
Sheffield Island Lighthouse
Fairfield Museum and History Center ©
Fairfield Museum and History Center

1
night
Redding

Redding ©
Redding is a town in Fairfield County, Connecticut, United States. Your day by day itinerary now includes Weir Farm National Historic Site as well as Lake Zoar. Kick off your visit on the 15th (Tue): tour the pleasant surroundings at Weir Farm National Historic Site and then contemplate the waterfront views at Lake Zoar.

To find maps, ratings, other places to visit, and more tourist information, read Redding day trip planning app.

Redding is just a stone's throw from Norwalk. Expect a bit cooler evenings in Redding when traveling from Norwalk in August, with lows around 60°F. Finish your sightseeing early on the 16th (Wed) to allow enough time to travel to Danbury.

Things to do in Redding

Nature · Parks · Museums

Side Trips

Weir Farm National Historic Site, Lake Zoar
Highlights from your plan
Weir Farm National Historic Site ©
Weir Farm National Historic Site
Lake Zoar ©
Lake Zoar

1
night
Danbury

Danbury ©
Danbury is a city in northern Fairfield County, Connecticut, United States, located along the Still River approximately 70 miles northeast of New York City. On the 16th (Wed), get engrossed in the history at Danbury Museum & Historical Society and then tee off at Richter Park Golf Course.

For where to stay, traveler tips, maps, and more tourist information, use the Danbury trip itinerary maker website.

Danbury is just a stone's throw from Redding. In August, daily temperatures in Danbury can reach 80°F, while at night they dip to 60°F. Finish your sightseeing early on the 17th (Thu) to allow enough time to travel to Sherman.

Things to do in Danbury

Outdoors · Golf · Museums
Highlights from your plan
Richter Park Golf Course ©
Richter Park Golf Course
Danbury Museum & Historical Society ©
Danbury Museum & Historical Society

1
night
Sherman

Sherman ©
Sherman is the northernmost and least populous town of Fairfield County, Connecticut, United States. Kick off your visit on the 17th (Thu): see the interesting displays at Connecticut Antique Machinery, take a stroll through Hopkins Vineyard, and then learn about winemaking at White Silo Farm & Winery.

To see maps, photos, and other tourist information, read Sherman trip itinerary planner.

Sherman is very close to Danbury. In August, daily temperatures in Sherman can reach 80°F, while at night they dip to 60°F. Finish your sightseeing early on the 18th (Fri) to allow enough time to travel to Milford.

Things to do in Sherman

Wineries · Neighborhoods · Museums

Side Trips

Hopkins Vineyard, Connecticut Antique Machinery
Highlights from your plan
White Silo Farm & Winery ©
White Silo Farm & Winery
Connecticut Antique Machinery ©
Connecticut Antique Machinery

2
nights
Milford

Milford ©
Milford is a Coterminous municipality within Coastal Connecticut and New Haven County, Connecticut, between Bridgeport, Connecticut and New Haven, Connecticut. Start off your visit on the 18th (Fri): do a tasting at Laurel Lake Vineyard, then stroll the grounds of Calverton National Cemetery, and then look for gifts at Amazing Olive. On the 19th (Sat), you'll have a packed day of sightseeing: immerse yourself in nature at Silver Sands State Park and then get engrossed in the history at Boothe Memorial Park and Museum.

For other places to visit, photos, and tourist information, you can read our Milford trip planner.

Drive from Sherman to Milford in 1.5 hours. Traveling from Sherman in August, Milford is somewhat warmer at night with lows of 67°F. Finish your sightseeing early on the 20th (Sun) so you can drive to New Haven.

Things to do in Milford

Nature · Parks · Museums

Side Trips

Boothe Memorial Park and Museum, Calverton National Cemetery, Amazing Olive, Laurel Lake Vineyard
Highlights from your plan
Silver Sands State Park ©
Silver Sands State Park
Laurel Lake Vineyard ©
Laurel Lake Vineyard
Boothe Memorial Park and Museum ©
Boothe Memorial Park and Museum

4
nights
New Haven

New Haven ©
New Haven, in the U.S. You'll explore the less-touristy side of things at Meschutt Beach and Grove Street Cemetery. Bidwell House Museum and William Floyd Estate are good opportunities to explore the local culture. Get out of town with these interesting New Haven side-trips: Shinnecock East County Park (in Southampton), Roanoke Vineyards (in Riverhead) and Shinn Estate Vineyards (in Mattituck). Next up on the itinerary: admire the masterpieces at Yale University Art Gallery.

Find out how to plan New Haven trip without stress by asking Inspirock to help create an itinerary.

New Haven is just a short distance from Milford. In August, daily temperatures in New Haven can reach 81°F, while at night they dip to 65°F. Wrap up your sightseeing on the 24th (Thu) to allow time to drive to Hartford.

Things to do in New Haven

Outdoors · Beaches · Parks

Side Trips

Southampton, William Floyd Estate, Bidwell House Museum, Roanoke Vineyards, Shinn Estate Vineyards
Highlights from your plan
Bidwell House Museum ©
Bidwell House Museum
Meschutt Beach ©
Meschutt Beach
Grove Street Cemetery ©
Grove Street Cemetery

1
night
Hartford

Hartford ©
Hartford is the capital of the U.S. On the 24th (Thu), appreciate the extensive heritage of Old Wethersfield and then explore the galleries of The Mark Twain House & Museum.

To see reviews, ratings, and tourist information, you can read our Hartford tour itinerary site.

Traveling by car from New Haven to Hartford takes an hour. Alternatively, you can take a train; or take a bus. In August, daytime highs in Hartford are 83°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 25th (Fri) to allow time to drive to Haddam.

Things to do in Hartford

Historic Sites · Museums

Side Trip

Old Wethersfield
Highlights from your plan
Old Wethersfield ©
Old Wethersfield
The Mark Twain House & Museum ©
The Mark Twain House & Museum

1
night
Haddam

Haddam ©
Haddam is a town in Middlesex County, Connecticut, United States. Kick off your visit on the 25th (Fri): do a tasting at Arrigoni Winery.

For maps, ratings, where to stay, and other tourist information, use the Haddam trip planner.

Haddam is very close to Hartford. August in Haddam sees daily highs of 79°F and lows of 63°F at night. Wrap up your sightseeing by early afternoon on the 26th (Sat) to allow time for travel to Colchester.

Things to do in Haddam

Wineries

Side Trip

Arrigoni Winery
Highlights from your plan
Arrigoni Winery ©
Arrigoni Winery

1
night
Colchester

Colchester ©
Colchester is a town in New London County, Connecticut, United States. Kick off your visit on the 26th (Sat): immerse yourself in nature at Devil's Hopyard State Park and then learn about winemaking at Priam Vineyards.

For more things to do, other places to visit, reviews, and more tourist information, read our Colchester trip itinerary builder app.

Colchester is just a short distance from Haddam. In August in Colchester, expect temperatures between 82°F during the day and 60°F at night. Wrap up your sightseeing on the 27th (Sun) to allow time to travel to Niantic.

Things to do in Colchester

Nature · Parks · Wineries

Side Trip

Devil's Hopyard State Park
Highlights from your plan
Devil's Hopyard State Park ©
Devil's Hopyard State Park
Priam Vineyards ©
Priam Vineyards

1
night
Niantic

Niantic ©
Niantic is a census-designated place (CDP) and village in the town of East Lyme, Connecticut in the United States. Kick off your visit on the 27th (Sun): kick back and relax at Hole-in-the-Wall Beach, explore the world behind art at Florence Griswold Museum, and then look for gifts at The Book Barn.

For maps, other places to visit, and tourist information, read Niantic trip planner.

Drive from Colchester to Niantic in an hour. In August in Niantic, expect temperatures between 79°F during the day and 63°F at night. Wrap up your sightseeing on the 28th (Mon) early enough to travel to Groton.

Things to do in Niantic

Outdoors · Beaches · Parks

Side Trips

Florence Griswold Museum, Hole-in-the-Wall Beach
Highlights from your plan
Florence Griswold Museum ©
Florence Griswold Museum
The Book Barn ©
The Book Barn

2
nights
Groton

Groton ©
Groton is a town located on the Thames River in New London County, Connecticut, United States. Start off your visit on the 28th (Mon): stroll through Eastern Point Beach and then admire the majestic nature at Fort Trumbull State Park. Keep things going the next day: examine the collection at United States Coast Guard Museum and then visit a coastal fixture at New London Ledge Light.

To see other places to visit, where to stay, reviews, and other tourist information, read our Groton day trip site.

Groton is very close to Niantic. August in Groton sees daily highs of 79°F and lows of 63°F at night. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive to Mystic.

Things to do in Groton

Parks · Historic Sites · Outdoors

Side Trip

New London
Highlights from your plan
Eastern Point Beach ©
Eastern Point Beach
Fort Trumbull State Park ©
Fort Trumbull State Park
New London Ledge Light ©
New London Ledge Light

3
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Popular historic sites such as Beavertail Lighthouse and Park and Stonington Lighthouse Museum are in your itinerary. Relax by the water at Watch Hill Beach and Third Beach. Step out of Mystic to go to Middletown and see Sweet Berry Farm, which is approximately 1h 10 min away.

To find photos, other places to visit, traveler tips, and more tourist information, read our Mystic trip website.

Mystic is just a stone's throw from Groton. In August, daily temperatures in Mystic can reach 79°F, while at night they dip to 63°F. Finish up your sightseeing early on the 2nd (Sat) so you can go by car to Branford.

Things to do in Mystic

Parks · Outdoors · Beaches

Side Trips

Middletown, Beavertail Lighthouse and Park, Watch Hill Beach, Stonington Lighthouse Museum
Highlights from your plan
Watch Hill Beach ©
Watch Hill Beach
Beavertail Lighthouse and Park ©
Beavertail Lighthouse and Park
Stonington Lighthouse Museum ©
Stonington Lighthouse Museum

1
night
Branford

Branford ©
Branford is a shoreline town located on Long Island Sound in New Haven County, Connecticut, 8mi east of New Haven. Start off your visit on the 2nd (Sat): examine the collection at Shore Line Trolley Museum, then sample the tasty concoctions at Thimble Islands Brewing Company, and then enjoy the sand and surf at Hammonasset Beach State Park.

To find where to stay, more things to do, traveler tips, and other tourist information, read Branford day trip tool.

You can drive from Mystic to Branford in an hour. Other options are to take a train; or do a combination of train and bus. September in Branford sees daily highs of 77°F and lows of 59°F at night. Wrap up your sightseeing by early afternoon on the 3rd (Sun) to allow time for the car ride back home.

Things to do in Branford

Outdoors · Beaches · Nature

Side Trips

Hammonasset Beach State Park, Lenz Winery, Shore Line Trolley Museum
Highlights from your plan
Shore Line Trolley Museum ©
Shore Line Trolley Museum
Lenz Winery ©
Lenz Winery
Hammonasset Beach State Park ©
Hammonasset Beach State Park

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