10 days in Connecticut, Hyde Park & Irvington Itinerary

10 days in Connecticut, Hyde Park & Irvington Itinerary

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Route & dates

10 days in Connecticut, Hyde Park & Irvington Itinerary

Start: Bridgeport
Drive:  30​min
1
New Haven
— 1 day
Drive:  1​h
2
Mystic
— 2 nights
Drive:  1​h
3
Middletown
— 2 nights
Drive:  2​h
4
Hyde Park
— 3 nights
Drive:  1​h 30​min
5
Irvington
— 2 nights
Drive:  1​h
End: Bridgeport

1
day
New Haven

New Haven ©
New Haven, in the U.S. Your list of things to see and do now includes Home of Franklin D. Roosevelt, St. Mary's Church, Edgerton Park, and other attractions. Start off your visit on the 12th (Sat): pause for some serene contemplation at St. Mary's Church, stroll around Edgerton Park, then contemplate the long history of Home of Franklin D. Roosevelt, then explore the world behind art at Norman Rockwell Museum, and finally learn about winemaking at Gouveia Vineyards.

To find maps, more things to do, reviews, and other tourist information, you can read our New Haven trip builder tool .

Bridgeport to New Haven is an approximately half hour car ride. Expect a daytime high around 66°F in October, and nighttime lows around 48°F. Finish up your sightseeing early on the 12th (Sat) so you can go by car to Mystic.

Things to do in New Haven

Historic Sites Parks Wineries

Side Trips

Home of Franklin D. Roosevelt, Norman Rockwell Museum, Gouveia Vineyards
Highlights from your plan
Home of Franklin D. Roosevelt ©
Home of Franklin D. Roosevelt
Norman Rockwell Museum ©
Norman Rockwell Museum
St. Mary's Church ©
St. Mary's Church

2
nights
Mystic

Mystic ©
A historical leading seaport, Mystic has maintained a strong respect for the past.
Kick off your visit on the 13th (Sun): meet the residents at Mystic Aquarium, then contemplate the long history of Olde Mistick Village, then examine the collection at Mystic Seaport Museum, and finally take an in-depth tour of Tantaquidgeon Museum. Here are some ideas for day two: take in the views from Mystic River Bascule Bridge, go for a walk through Mystic River Historical Society, then examine the collection at The Submarine Force Museum, and finally try to win big at Foxwoods Resort Casino.

For photos, maps, reviews, and tourist information, read our Mystic trip itinerary builder app .

You can drive from New Haven to Mystic in an hour. Other options are to take a train; or take a bus. October in Mystic sees daily highs of 65°F and lows of 48°F at night. Cap off your sightseeing on the 14th (Mon) early enough to go by car to Middletown.

Things to do in Mystic

Museums Fun & Games Casinos

Side Trips

The Submarine Force Museum, Foxwoods Resort Casino, Tantaquidgeon Museum
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum
Mystic Aquarium ©
Mystic Aquarium
Olde Mistick Village ©
Olde Mistick Village

2
nights
Middletown

Middletown ©
Middletown is a city located in Middlesex County, Connecticut, along the Connecticut River, in the central part of the state, 16 miles (26 km) south of Hartford. Wadsworth Falls State Park has been added to your itinerary. Kick off your visit on the 15th (Tue): brush up on your knowledge of spirits at Onyx Moonshine, explore the galleries of The Mark Twain House & Museum, and then grab your bike and head to Wadsworth Falls State Park. Get ready for a full day of sightseeing on the 16th (Wed): have fun and explore at Kidcity Children's Museum, hike along Cotton Hollow Preserve, and then get in on the family fun at Six Flags New England.

Take the guesswork out of planning a Middletown vacation by using our trip itinerary maker.

You can drive from Mystic to Middletown in an hour. In October in Middletown, expect temperatures between 67°F during the day and 44°F at night. Wrap up your sightseeing on the 16th (Wed) early enough to drive to Hyde Park.

Things to do in Middletown

Parks Outdoors Trails

Side Trips

Onyx Moonshine, Six Flags New England, The Mark Twain House & Museum, Cotton Hollow Preserve
Highlights from your plan
Wadsworth Falls State Park ©
Wadsworth Falls State Park
The Mark Twain House & Museum ©
The Mark Twain House & Museum
Kidcity Children's Museum ©
Kidcity Children's Museum

3
nights
Hyde Park

Hyde Park ©
Hyde Park is a town in Dutchess County, New York, bordering the Hudson River north of Poughkeepsie. You've now added Vanderbilt Mansion National Historic Site to your itinerary. On the 17th (Thu), don't miss a visit to G. Steve Jordan Gallery, snap pictures at Walkway Over the Hudson State Historic Park, get engrossed in the history at Franklin D. Roosevelt Presidential Library and Museum, then contemplate the long history of Vanderbilt Mansion National Historic Site, and finally steep yourself in history at Eleanor Roosevelt National Historic Site. On the next day, immerse yourself in nature at Minnewaska State Park Preserve and then experience rural life at Hancock Shaker Village.

For traveler tips, other places to visit, photos, and more tourist information, go to the Hyde Park online attractions planner .

You can drive from Middletown to Hyde Park in 2 hours. In October, daytime highs in Hyde Park are 67°F, while nighttime lows are 43°F. Wrap up your sightseeing by early afternoon on the 19th (Sat) to allow time for the car ride to Irvington.

Things to do in Hyde Park

Historic Sites Museums Parks

Side Trips

Minnewaska State Park Preserve, G. Steve Jordan Gallery, Pride of the Hudson, Walkway Over the Hudson State Historic Park, Hancock Shaker Village
Highlights from your plan

2
nights
Irvington

Irvington ©
Irvington, sometimes known as Irvington-on-Hudson, is an affluent suburban village in the town of Greenburgh in Westchester County, New York, United States. Washington Irving's Sunnyside House has been added to your itinerary. On the 19th (Sat), contemplate the long history of Washington Irving's Sunnyside House and then stroll around Matthiessen Park. Get ready for a full day of sightseeing on the next day: explore the activities along Marshlands Conservancy, then take a memorable drive along Palisades Interstate Park Commission: State Line Lookout, then relax in the rural setting at Demarest Farm, and finally take an in-depth tour of The DeWint House.

To see reviews, maps, where to stay, and more tourist information, refer to the Irvington online vacation planner .

You can drive from Hyde Park to Irvington in 1.5 hours. Expect a bit warmer evenings in Irvington when traveling from Hyde Park in October, with lows around 49°F. You will leave for home on the 21st (Mon).

Things to do in Irvington

Scenic Drive Outdoors Parks

Side Trips

Palisades Interstate Park Commission: State Line Lookout, Demarest Farm, The DeWint House, Marshlands Conservancy
Highlights from your plan

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