9 days in Ogunquit, DownEast and Acadia Maine & Rockland Itinerary

9 days in Ogunquit, DownEast and Acadia Maine & Rockland Itinerary

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Route & dates

9 days in Ogunquit, DownEast and Acadia Maine & Rockland Itinerary

Start: Chicago
+2
Fly + taxi + bus:  6​h 30​min
1
Ogunquit
— 4 nights
Drive:  3​h 45​min
2
Winter Harbor
— 1 night
Drive:  1​h
3
Bar Harbor, Mount Desert Island
— 2 nights
Drive:  2​h 15​min
4
Rockland
— 1 night
Fly:  7​h
End: Chicago

4
nights
Ogunquit

Ogunquit ©
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Escape the urban bustle at Ogunquit Beach and Perkins Cove. Do your shopping at L.L. Bean Factory Store and Abacus. You'll find plenty of places to visit near Ogunquit: Hampton Beach State Park (in Hampton), Dolphin & Whale Watching (in Gloucester) and W. Robert Paine Gallery (in Kennebunkport). There's much more to do: appreciate the extensive heritage of Marginal Way Walkway, immerse yourself in nature at Popham Beach State Park, kick back and relax at Old Orchard Beach, and tour the pleasant surroundings at Wells Beach.

To find photos, where to stay, ratings, and more tourist information, read our Ogunquit online tour planner .

Chicago to Ogunquit is an approximately 6.5-hour combination of flight and bus. You can also drive; or take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Prepare for little chillier weather when traveling from Chicago in May: high temperatures in Ogunquit hover around 66°F and lows are around 43°F. Finish your sightseeing early on the 2nd (Sun) so you can travel to Winter Harbor.

Things to do in Ogunquit

Outdoors Parks Beaches

Side Trips

L.L. Bean Factory Store, Hampton Beach State Park, Wells Beach, Popham Beach State Park, Old Orchard Beach
Highlights from your plan
Ogunquit Beach ©
Ogunquit Beach
Dolphin & Whale Watching
Marginal Way Walkway ©
Marginal Way Walkway

1
night
Winter Harbor

Winter Harbor ©
Not to be confused with Winter Harbor, Maine the former name of Biddeford PoolWinter Harbor is a town on the Schoodic Peninsula in Hancock County, Maine, United States. Start off your visit on the 3rd (Mon): look for gifts at US Bells, take in the exciting artwork at Chapter Two Art Gallery, explore the striking landscape at Schoodic Point, then view the masterpieces at Works of Hand, and finally shop like a local with Whopaints Gallery.

To see maps, photos, other places to visit, and other tourist information, you can read our Winter Harbor day trip planner .

Drive from Ogunquit to Winter Harbor in 4 hours. While traveling from Ogunquit, expect little chillier days and about the same nights in Winter Harbor, ranging from highs of 68°F to lows of 52°F. Cap off your sightseeing on the 3rd (Mon) early enough to go by car to Bar Harbor.

Things to do in Winter Harbor

Shopping Museums Parks

Side Trips

US Bells, Chapter Two Art Gallery
Highlights from your plan
US Bells ©
US Bells
Whopaints Gallery ©
Whopaints Gallery

2
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. On the 4th (Tue), tour the pleasant surroundings at Sand Beach, look for gifts at Bar Harbor Popcorn, and then take in the awesome beauty at Cadillac Mountain. Get ready for a full day of sightseeing on the 5th (Wed): take in the exciting artwork at Little Village Gifts, then identify plant and animal life at Shore Path, and then head off the coast to Mount Desert Island.

To see other places to visit, ratings, more things to do, and tourist information, read Bar Harbor tour itinerary maker tool .

You can drive from Winter Harbor to Bar Harbor in an hour. In June, daily temperatures in Bar Harbor can reach 68°F, while at night they dip to 52°F. Cap off your sightseeing on the 5th (Wed) early enough to go by car to Rockland.

Things to do in Bar Harbor

Parks Nature Outdoors

Side Trip

Acadia National Park
Highlights from your plan
Mount Desert Island ©
Mount Desert Island
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 6th (Thu): admire the masterpieces at Farnsworth Art Museum, then see the interesting displays at Owls Head Transportation Museum, then visit a coastal fixture at Rockland Breakwater Light, and finally stop by Maine State Prison Store.

To see ratings, other places to visit, and other tourist information, use the Rockland sightseeing planning website .

Drive from Bar Harbor to Rockland in 2.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Rockland can reach 68°F, while at night they dip to 51°F. Finish up your sightseeing early on the 6th (Thu) so you can travel back home.

Things to do in Rockland

Museums Historic Sites Shopping

Side Trips

Maine State Prison Store, Owls Head Transportation Museum
Highlights from your plan
Farnsworth Art Museum ©
Farnsworth Art Museum
Owls Head Transportation Museum ©
Owls Head Transportation Museum
Maine State Prison Store ©
Maine State Prison Store

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