22 days in Connecticut Itinerary

22 days in Connecticut Itinerary

Created using Inspirock Connecticut Trip Planner

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Route & dates

22 days in Connecticut Itinerary

Start: New York City
Drive:  1​h 15​min
1
Stamford
— 1 night
Drive:  30​min
2
Norwalk
— 1 night
Drive:  30​min
3
Redding
— 1 night
Drive:  30​min
4
Danbury
— 1 night
Drive:  30​min
5
Sherman
— 1 night
Drive:  1​h
6
Milford
— 2 nights
Drive:  30​min
7
New Haven
— 4 nights
Drive:  45​min
8
Hartford
— 1 night
Drive:  45​min
9
Haddam
— 1 night
Drive:  30​min
10
Colchester
— 1 night
Drive:  45​min
11
Niantic
— 1 night
Drive:  30​min
12
Groton
— 2 nights
Drive:  30​min
13
Mystic
— 3 nights
Drive:  1​h
14
Branford
— 1 night
Drive:  1​h 45​min
End: New York City

1
night
Stamford

Stamford ©
Stamford is a city in Fairfield County, Connecticut, United States. Kick off your visit on the 13th (Sun): take an in-depth tour of Sagamore Hill National Historic Site and then admire the majestic nature at Caumsett State Park.

To find maps, reviews, ratings, and tourist information, use the Stamford vacation trip planner.

New York City to Stamford is an approximately 1-hour car ride. Traveling from New York City in August, you can expect nighttime temperatures to be little chillier in Stamford, with lows of 65°F. Wrap up your sightseeing on the 14th (Mon) to allow time to travel to Norwalk.

Things to do in Stamford

Parks Nature Museums

Side Trips

Caumsett State Park, Sagamore Hill National Historic Site
Highlights from your plan
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): visit a coastal fixture at Sheffield Island Lighthouse, get engrossed in the history at Fairfield Museum and History Center, and then relax and rejuvenate at some of the top local wellness centers.

To find other places to visit, reviews, traveler tips, and other tourist information, read our Norwalk online itinerary creator.

Norwalk is just a short distance from Stamford. In August, daytime highs in Norwalk are 82°F, while nighttime lows are 67°F. Finish your sightseeing early on the 15th (Tue) so you can 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 ©

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): explore the striking landscape of Weir Farm National Historic Site and then explore the activities along Lake Zoar.

To see traveler tips, other places to visit, photos, and tourist information, go to the Redding vacation planner.

Redding is very close to Norwalk. Traveling from Norwalk in August, you can expect nighttime temperatures to be a bit cooler in Redding, with lows of 61°F. Finish up your sightseeing early on the 16th (Wed) so you can travel to Danbury.

Things to do in Redding

Parks Nature 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. Start off your visit on the 16th (Wed): take an in-depth tour of Danbury Museum & Historical Society and then play a few rounds at Richter Park Golf Course.

To see reviews, maps, other places to visit, and more tourist information, read Danbury online itinerary creator.

Danbury is very close to Redding. In August, daytime highs in Danbury are 80°F, while nighttime lows are 61°F. Finish your sightseeing early on the 17th (Thu) so you can 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 ©

1
night
Sherman

Sherman ©
Sherman is the northernmost and least populous town of Fairfield County, Connecticut, United States. Start off your visit on the 17th (Thu): examine the collection at Connecticut Antique Machinery, then wander the streets of Hopkins Vineyard, and then relax in the rural setting at White Silo Farm & Winery.

For where to stay, reviews, other places to visit, and more tourist information, go to the Sherman tour planner.

Sherman is just a short distance from Danbury. In August, daytime highs in Sherman are 80°F, while nighttime lows are 61°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. On the 18th (Fri), learn about winemaking at Laurel Lake Vineyards, stroll the grounds of Calverton National Cemetery, and then look for gifts at Amazing Olive. Keep things going the next day: immerse yourself in nature at Silver Sands State Park and then get engrossed in the history at Boothe Memorial Park and Museum.

To see traveler tips, reviews, more things to do, and more tourist information, read Milford tour planner.

You can drive from Sherman to Milford in 1.5 hours. Expect somewhat warmer evenings in Milford when traveling from Sherman in August, with lows around 67°F. Wrap up your sightseeing on the 20th (Sun) to allow time to travel to New Haven.

Things to do in Milford

Parks Nature Museums

Side Trips

Amazing Olive, Calverton National Cemetery, Laurel Lake Vineyard, Boothe Memorial Park and Museum
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. Discover out-of-the-way places like Yale University Art Gallery and William Floyd Estate. Your itinerary includes some good beach time at Meschutt Beach and Shinnecock East County Park. Change things up with these side-trips from New Haven: Shinn Estate Vineyards and Farmhouse (in Mattituck) and Bidwell House Museum (in Monterey). There's more to do: stroll the grounds of Grove Street Cemetery and do a tasting at Roanoke Vineyards.

To find photos, more things to do, reviews, and other tourist information, refer to the New Haven vacation builder.

New Haven is just a short distance from Milford. August in New Haven sees daily highs of 81°F and lows of 65°F at night. Finish your sightseeing early on the 24th (Thu) so you can drive to Hartford.

Things to do in New Haven

Outdoors Parks Beaches

Side Trips

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

1
night
Hartford

Hartford ©
Hartford is the capital of the U.S. Kick off your visit on the 24th (Thu): appreciate the extensive heritage of Old Wethersfield and then contemplate the long history of Mark Twain House & Museum.

To see photos, reviews, ratings, and other tourist information, go to the Hartford trip itinerary maker.

You can drive from New Haven to Hartford in an hour. Other options are to take a bus; or take a train. In August, daytime highs in Hartford are 83°F, while nighttime lows are 64°F. Finish your sightseeing early on the 25th (Fri) so you can travel 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. On the 25th (Fri), do a tasting at Arrigoni Winery and then let the river carry you with a rafting and tubing tour.

To see ratings, more things to do, traveler tips, and tourist information, refer to the Haddam trip generator.

You can drive from Hartford to Haddam in an hour. In August, daytime highs in Haddam are 79°F, while nighttime lows are 63°F. Cap off your sightseeing on the 26th (Sat) early enough to 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. Start off your visit on the 26th (Sat): immerse yourself in nature at Devil's Hopyard State Park and then do a tasting at Priam Vineyards.

To find more things to do, traveler tips, and more tourist information, go to the Colchester tour planner.

Colchester is very close to Haddam. In August in Colchester, expect temperatures between 79°F during the day and 63°F at night. Wrap up your sightseeing on the 27th (Sun) to allow time to travel to Niantic.

Things to do in Colchester

Parks Nature 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. Start off your visit on the 27th (Sun): enjoy the sand and surf at Hole-in-the-Wall Beach, then explore the world behind art at Florence Griswold Museum, and then look for gifts at The Book Barn.

To find where to stay, maps, photos, and more tourist information, use the Niantic sightseeing planner.

You can drive from Colchester to Niantic in an hour. In August in Niantic, expect temperatures between 78°F during the day and 64°F at night. Finish your sightseeing early on the 28th (Mon) to allow enough time to travel to Groton.

Things to do in Niantic

Outdoors Parks Beaches

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. Kick off your visit on the 28th (Mon): stroll through Eastern Point Beach and then immerse yourself in nature at Fort Trumbull State Park. Keep things going the next day: soothe aching muscles at some of the top local wellness centers, see the interesting displays at United States Coast Guard Academy, and then visit a coastal fixture at New London Ledge Light.

For reviews, ratings, and other tourist information, read Groton itinerary planner.

Groton is just a short distance from Niantic. In August, plan for daily highs up to 78°F, and evening lows to 64°F. Finish up your sightseeing early on the 30th (Wed) so you can travel 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.
We've included these beaches for you: Watch Hill Beach and Third Beach. Get some historical perspective at Beavertail Lighthouse and Park and Old Lighthouse Museum. Step out of Mystic to go to Middletown and see Sweet Berry Farm, which is approximately 1h 10 min away.

To find maps, other places to visit, and tourist information, go to the Mystic trip planner.

Mystic is just a stone's throw from Groton. August in Mystic sees daily highs of 78°F and lows of 64°F at night. Cap off your sightseeing on the 2nd (Sat) early enough to go by car to Branford.

Things to do in Mystic

Parks Outdoors Beaches

Side Trips

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

1
night
Branford

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

To see where to stay, ratings, more things to do, and other tourist information, refer to the Branford trip itinerary maker.

Traveling by car from Mystic to Branford takes an hour. Alternatively, you can take a train; or take a bus. In September, plan for daily highs up to 74°F, and evening lows to 58°F. On the 3rd (Sun), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Branford

Outdoors Parks Nature

Side Trips

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

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