14 days in Boston, Maine & Stockbridge Itinerary

14 days in Boston, Maine & Stockbridge Itinerary

Created using Inspirock United States trip itinerary maker

Plan created by another user. Make it yours
1
Boston
— 1 night
2
Kennebunkport
— 2 nights
3
Rockland
— 2 nights
4
Bar Harbor, Mount Desert Island
— 4 nights
5
Bangor
— 2 nights
6
Boston
— 1 night
7
Stockbridge
— 1 night

S M T W T F S
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1
night
Boston

Boston ©

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.
On the 10th (Sat), admire the masterpieces at Boston Athenaeum, then browse the collection at The Mary Baker Eddy Library, then learn about all things military at USS Cassin Young, and finally shop like a local with Boston Public Market.

For photos, maps, traveler tips, and more tourist information, use the Boston trip builder app.

Middlebury to Boston is an approximately 2.5-hour car ride. Expect a daytime high around 81°F in August, and nighttime lows around 65°F. Finish your sightseeing early on the 10th (Sat) so you can drive to Kennebunkport.

Things to do in Boston

Highlights from your plan
USS Cassin Young ©
USS Cassin Young
Boston Athenaeum ©
Boston Athenaeum
Boston Public Market ©
Boston Public Market

2
nights
Kennebunkport

Kennebunkport ©
Kennebunkport is a town in York County, Maine, United States. Kick off your visit on the 10th (Sat): look for gifts at Scalawags Pet Boutique and then view the masterpieces at Compliments. On the 11th (Sun), you'll have a packed day of sightseeing: stroll through Mother's Beach, kick back and relax at Gooch's Beach, then take a memorable drive along St. Anthony's Monastery, and finally appreciate the extensive heritage of Parson's Way.

For traveler tips, maps, other places to visit, and more tourist information, refer to the Kennebunkport vacation planner.

Getting from Boston to Kennebunkport by car takes about 2 hours. Other options: take a bus; or do a combination of train and bus. Expect slightly colder evenings in Kennebunkport when traveling from Boston in August, with lows around 54°F. Wrap up your sightseeing on the 12th (Mon) early enough to drive to Rockland.

Things to do in Kennebunkport

Parks · Outdoors · Beaches · Wildlife

Side Trips

Highlights from your plan
Drakes Island Beach ©
Drakes Island Beach
Wells Reserve at Laudholm ©
Wells Reserve at Laudholm
First Families Kennebunkport Museum ©
First Families Kennebunkport Museum

2
nights
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Start off your visit on the 13th (Tue): identify plant and animal life at Todd Audubon Sanctuary at Hog Island, immerse yourself in nature at Owl's Head State Park, and then kick back and relax at Sandy Beach. On your second day here, steep yourself in history at General Henry Knox Museum / Montpelier, examine the collection at Sail Power and Steam Museum, then explore the engaging exhibits at Coastal Children's Museum, then stop by Fiore Artisan Olive Oils and Vinegars, and finally explore the world behind art at Olson House.

To find where to stay, more things to do, maps, and other tourist information, use the Rockland road trip website.

Drive from Kennebunkport to Rockland in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Kennebunkport in August, you will find days in Rockland are little chillier (74°F), and nights are about the same (56°F). Finish your sightseeing early on the 14th (Wed) so you can drive to Bar Harbor.

Things to do in Rockland

Parks · Museums · Nature · Outdoors

Side Trips

Highlights from your plan
Owl's Head State Park ©
Owl's Head State Park
Olson House ©
Olson House
Sail Power and Steam Museum ©
Sail Power and Steam Museum

4
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Bring the kids along to Agamont Park and St. Saviour's Church :. Eschew the tourist crowds and head to The Seal Cove Auto Museum and Ship Harbor Nature Trail. Take a break from Bar Harbor with a short trip to Wonderland Trail in Southwest Harbor, about 32 minutes away. Next up on the itinerary: stroll around Charlotte Rhoades Garden and Butterfly Park, enjoy the sea views from Egg Rock Light, hike along Flying Mountain Hiking Trail, and stop by The Christmas Vacation Shop.

To find more things to do, photos, and other tourist information, refer to the Bar Harbor trip itinerary site.

Drive from Rockland to Bar Harbor in 2.5 hours. Alternatively, you can take a bus. In August, daily temperatures in Bar Harbor can reach 75°F, while at night they dip to 57°F. Wrap up your sightseeing by early afternoon on the 18th (Sun) to allow enough time to take a shuttle to Bangor.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Wildlife

Side Trips

Highlights from your plan
The Seal Cove Auto Museum ©
The Seal Cove Auto Museum
Wonderland Trail ©
Wonderland Trail
Ship Harbor Nature Trail ©
Ship Harbor Nature Trail

2
nights
Bangor

Bangor ©
Bangor is a city along the Penobscot River in the U.S. Kick off your visit on the 18th (Sun): take in the exciting artwork at Wild Mountain Man Ray's Chainsaw Show. Get ready for a full day of sightseeing on the 19th (Mon): grab your bike and head to Penobscot River Walkway, brush up on your military savvy at Bangor Historical Society and Thomas A. Hill House Museum, then identify plant and animal life at Orono Bog Boardwalk, and finally grab your bike and head to Bangor City Forest.

Plan a trip to Bangor easily and quickly by telling Inspirock to suggest an itinerary.

You can take a shuttle from Bar Harbor to Bangor in 1.5 hours. Other options are to drive; or take a bus. August in Bangor sees daily highs of 79°F and lows of 57°F at night. Wrap up your sightseeing on the 20th (Tue) to allow time to drive to Boston.

Things to do in Bangor

Parks · Museums · Outdoors · Trails

Side Trips

Highlights from your plan
Orono Bog Boardwalk ©
Orono Bog Boardwalk
Penobscot Marine Museum
Penobscot Marine Museum
Bangor City Forest ©
Bangor City Forest

1
night
Boston

Boston ©

Beantown

Kick off your visit on the 21st (Wed): contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, pause for some serene contemplation at King's Chapel, then walk around Rose Kennedy Greenway, then pause for some serene contemplation at The First Church of Christ, Scientist, and finally explore the galleries of Buckman Tavern.

Ask Inspirock to suggest an itinerary and make planning a trip to Boston fast, fun, and easy.

Getting from Bangor to Boston by car takes about 4 hours. Other options: fly; or take a bus. Plan for a bit warmer nights when traveling from Bangor in August since evenings lows in Boston dip to 65°F. Finish your sightseeing early on the 21st (Wed) so you can drive to Stockbridge.

Things to do in Boston

Historic Sites · Parks · Museums

Side Trip

Highlights from your plan

1
night
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Plan a trip to Stockbridge easily and quickly by telling Inspirock to suggest an itinerary.

You can drive from Boston to Stockbridge in 2.5 hours. Other options are to take a bus; or take a train. Traveling from Boston in August, Stockbridge is slightly colder at night with lows of 55°F. Finish up your sightseeing early on the 22nd (Thu) so you can go by car back home.

Things to do in Stockbridge

Historic Sites · Museums · Shopping

Side Trips

Highlights from your plan
Steepletop ©
Steepletop
Ozzie's Glass Gallery ©
Ozzie's Glass Gallery
Stockbridge Library, Museum & Archives ©
Stockbridge Library, Museum & Archives

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