8 days in Boston, Maine & Woodstock Itinerary

8 days in Boston, Maine & Woodstock Itinerary

Created using Inspirock United States trip maker

Plan created by another user. Make it yours
Fly
1
Boston
— 1 night
Drive
2
Ogunquit
— 2 nights
Drive
3
Portland
— 3 nights
Drive
4
Woodstock
— 1 night
Drive

S M T W T F S
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Boston

— 1 night

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Kick off your visit on the 1st (Wed): get to know the fascinating history of HarborWalk, learn about all things military at USS Cassin Young, then pause for some serene contemplation at King's Chapel, then get a sense of history and politics at Old State House, and finally contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill. Get ready for a full day of sightseeing on the next day: explore the different monuments and memorials at Sleepy Hollow Cemetery, then explore the galleries of Louisa May Alcott's Orchard House, then contemplate the long history of Buckman Tavern, and finally take in the history at Lexington Green.

For photos, maps, other places to visit, and tourist information, read our Boston trip tool.

New York City to Boston is an approximately 3.5-hour flight. You can also drive; or take a train. Plan for little chillier nights when traveling from New York City in July since evenings lows in Boston dip to 67°F. Finish up your sightseeing early on the 2nd (Thu) so you can go by car to Ogunquit.

Things to do in Boston

Historic Sites · Museums

Side Trips

Ogunquit

— 2 nights
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.
Start off your visit on the 3rd (Fri): get to know the fascinating history of Marginal Way Walkway, take a tour by water with Boat Tours & Water Sports, then take in the dramatic natural features at Perkins Cove, and finally get a taste of the local shopping with PANACHE FINE JEWELRY AND ART GALLERY. Get ready for a full day of sightseeing on the next day: get your bearings at Ogunquit Memorial Library, explore the world behind art at Ogunquit Museum of American Art, and then enjoy the sand and surf at Ogunquit Beach.

To plan Ogunquit vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Boston to Ogunquit by car takes about 1.5 hours. Other options: do a combination of train and taxi; or take a bus. Traveling from Boston in July, expect slightly colder with lows of 58°F in Ogunquit. Cap off your sightseeing on the 4th (Sat) early enough to go by car to Portland.

Things to do in Ogunquit

Parks · Outdoors · Museums · Historic Sites

Portland

— 3 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Start off your visit on the 5th (Sun): see the interesting displays at Umbrella Cover Museum, explore the world behind art at Portland Museum of Art, then have fun and explore at Children's Museum and Theatre of Maine, then indulge your thirst for a good beer at Rising Tide Brewing Company, and finally do a tasting at Maine Mead Works. Keep things going the next day: steep yourself in history at Fort Gorges, then enjoy the sand and surf at Willard Beach, and then visit a coastal fixture at Portland Breakwater Lighthouse.

To find reviews and other tourist information, read Portland online visit planner.

Getting from Ogunquit to Portland by car takes about an hour. Other options: take a bus; or do a combination of taxi and train. July in Portland sees daily highs of 79°F and lows of 61°F at night. Cap off your sightseeing on the 7th (Tue) early enough to travel to Woodstock.

Things to do in Portland

Historic Sites · Museums · Beaches · Parks

Side Trip

Woodstock

— 1 night
Woodstock is a town in Ulster County, New York, United States. Kick off your visit on the 7th (Tue): experience rural life at Sunfrost Farm, then contemplate in the serene atmosphere at Karma Triyana Dharmachakra Tibetan Buddhist Monastery, and then take in the awesome beauty at Overlook Mountain.

To see where to stay, ratings, more things to do, and other tourist information, you can read our Woodstock trip planning website.

Traveling by car from Portland to Woodstock takes 5 hours. Alternatively, you can do a combination of flight and car. When traveling from Portland in July, plan for somewhat warmer days in Woodstock, with highs around 85°F, while nights are about the same with lows around 64°F. On the 8th (Wed), you'll have the morning to explore before heading back home.

Things to do in Woodstock

Historic Sites · Parks · Nature

Side Trip

Maine travel guide

4.5
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.