44 days in Long Island, Springfield & Bangor Itinerary

44 days in Long Island, Springfield & Bangor Itinerary

Created using Inspirock United States trip planner

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Make it your trip
Drive
1
Fire Island
— 2 nights
Drive
2
Cutchogue
— 5 nights
Drive
3
Montauk
— 6 nights
Drive
4
Stony Brook
— 2 nights
+2
Drive to John F Kennedy International Airport, Fly to Ronald Reagan Washington National Airport, Drive to Springfield
5
Springfield
— 8 nights
Drive to Ronald Reagan Washington National Airport, Fly to Bangor
6
Bangor
— 20 nights
Fly

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Fire Island

— 2 nights
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Take a break from the city and head to Robert Moses State Park and The Sunken Forest. You'll discover tucked-away gems like Fire Island Lighthouse and Kismet Beach. Get out of town with these interesting Fire Island side-trips: Hampton Bays (Meschutt Beach & Ponquogue Beach).

To see other places to visit, ratings, where to stay, and tourist information, read Fire Island trip planner.

New York City to Fire Island is an approximately 2-hour car ride. In July, plan for daily highs up to 84°F, and evening lows to 69°F. Finish your sightseeing early on the 27th (Tue) to allow enough time to drive to Cutchogue.

Things to do in Fire Island

Parks · Outdoors · Beaches · Nature

Side Trip

Cutchogue

— 5 nights
Cutchogue is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. We've included these beaches for you: Cupsogue Beach County Park and Orient Beach State Park. Eschew the tourist crowds and head to Mashomack Preserve and Boat Tours & Water Sports. When in Cutchogue, make a side trip to see Shelter Island Historical Society in Shelter Island, approximately Shelter Island away. There's still lots to do: do a tasting at Bedell Cellars, relax in the rural setting at Lavender By The Bay, indulge your senses at some of the top wineries in the area, and sample some tasty brews at Brew Crew Cycles.

To see other places to visit, reviews, traveler tips, and tourist information, refer to the Cutchogue day trip planning app.

You can drive from Fire Island to Cutchogue in 2 hours. When traveling from Fire Island in July, plan for slightly colder days in Cutchogue, with highs around 79°F, while nights are about the same with lows around 67°F. Finish your sightseeing early on the 1st (Sun) to allow enough time to drive to Montauk.

Things to do in Cutchogue

Wineries · Outdoors · Tours · Parks

Side Trips

Montauk

— 6 nights
Montauk is a census-designated place (CDP) that includes the hamlet with the same name located in the town of East Hampton in Suffolk County, New York, on the eastern end of the South Shore of Long Island. Take a break from the city and head to Viking Fleet and Camp Hero State Park. Your itinerary includes some good beach time at Main Beach and Foster Memorial Beach. Explore Montauk's surroundings by going to LongHouse Reserve (in East Hampton), Wolffer Estate Vineyard (in Sagaponack) and Custom House Museum (in Sag Harbor). There's lots more to do: immerse yourself in nature at Montauk Point State Park, don't miss a visit to Montauk Point Lighthouse, contemplate the long history of Pollock-Krasner House and Study Center, and tee off at Montauk Downs State Park Golf Course.

To find maps, ratings, other places to visit, and other tourist information, use the Montauk trip itinerary planning website.

Traveling by car from Cutchogue to Montauk takes 1.5 hours. August in Montauk sees daily highs of 79°F and lows of 66°F at night. Wrap up your sightseeing on the 7th (Sat) early enough to drive to Stony Brook.

Things to do in Montauk

Parks · Outdoors · Beaches · Nature

Side Trips

Stony Brook

— 2 nights
Stony Brook is a hamlet and census-designated place (CDP) in the Town of Brookhaven in Suffolk County, New York, on the North Shore of Long Island. Kick off your visit on the 8th (Sun): look for all kinds of wild species at Bayard Cutting Arboretum, identify plant and animal life at Holtsville Ecology Site, and then stroll around Cortwood Landing County Park. On the next day, identify plant and animal life at Avalon Park & Preserve, then contemplate the long history of St. James General Store, then head off the coast to Fire Island National Seashore, and finally steep yourself in history at Setauket Neighborhood House.

To see more things to do, reviews, traveler tips, and tourist information, you can read our Stony Brook visit site.

Drive from Montauk to Stony Brook in 2 hours. August in Stony Brook sees daily highs of 82°F and lows of 66°F at night. Finish your sightseeing early on the 9th (Mon) to allow enough time to travel to Springfield.

Things to do in Stony Brook

Parks · Wildlife · Nature · Outdoors

Side Trips

Springfield

— 8 nights
Springfield is a census-designated place (CDP) in Fairfax County, Virginia, United States. Step off the beaten path and head to Wolf Trap National Park for the Performing Arts and Appalachian Trail. George Washington's Distillery & Gristmill and George Washington's Mount Vernon will appeal to history buffs. Get out of town with these interesting Springfield side-trips: Sugarloaf Mountain (in Dickerson), Ball's Bluff Battlefield and National Cemetery (in Leesburg) and Wild Hare Hard Cider (in Bluemont). There's much more to do: look for all kinds of wild species at Hidden Pond Nature Center, learn about winemaking at Rappahannock Cellars, contemplate the waterfront views at Lake Accotink Park, and walk around Burke Lake Park.

To find more things to do, maps, where to stay, and more tourist information, go to the Springfield trip maker website.

Use the Route module to find suitable travel options from Stony Brook to Springfield. Expect a daytime high around 84°F in August, and nighttime lows around 65°F. Wrap up your sightseeing on the 17th (Tue) early enough to travel to Bangor.

Things to do in Springfield

Parks · Historic Sites · Nature · Museums

Side Trips

Bangor

— 20 nights
Bangor is a city along the Penobscot River in the U.S. state of Maine. Escape the urban bustle at Cadillac Mountain and Boat Tours & Water Sports. Your inner history buff will appreciate Bass Harbor Head Lighthouse and Penobscot Marine Museum. Explore the numerous day-trip ideas around Bangor: Acadia National Park (Bubble Rock, Carriage Roads, &more), Bar Harbor (Cadillac Mountain North Ridge Trail, Compass Harbor Trail, &more) and Moose Point State Park (in Searsport). There's still lots to do: trek along Wonderland Trail, stroll through Flying Mountain Hiking Trail, do a tasting at Cellardoor Winery, and grab your bike and head to Penobscot River Walkway.

For more things to do, where to stay, photos, and more tourist information, read our Bangor road trip planning app.

Use the Route module to find suitable travel options from Springfield to Bangor. Expect a bit cooler temperatures when traveling from Springfield in August; daily highs in Bangor reach 79°F and lows reach 57°F. Cap off your sightseeing on the 6th (Mon) early enough to catch the flight back home.

Things to do in Bangor

Parks · Outdoors · Trails · Nature

Side Trips

Long Island travel guide

4.3
Wineries & Vineyards · Beaches · Lighthouses
Stretching northeast from New York Harbor to the Atlantic Ocean, Long Island is the largest island in the continental U.S. It technically includes the New York City boroughs of Brooklyn and Queens, but generally refers to the suburban counties of Nassau and Suffolk exclusively. Known for its cookie-cutter suburban neighborhoods, the island is also home to a wealth of intriguing places to visit, including beaches, scenic countryside, wineries, and numerous historical sites. In the summer months, wealthy New Yorkers flock here to relax in their exclusive Hamptons properties.