16 days in New England Itinerary

16 days in New England Itinerary

Created using Inspirock New England holiday builder

Make it your trip
Fly
1
Boston
— 3 nights
Fly
2
Bar Harbor, Mount Desert Island
— 3 nights
Drive
3
Portland
— 1 night
Drive
4
North Conway
— 3 nights
Drive
5
Lincoln
— 2 nights
Drive
6
Stowe
— 2 nights
Drive to Plattsburgh International Airport, Fly to Sofia

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Boston

— 3 nights

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.
Take a break from Boston with a short trip to Marginal Way Walkway in Ogunquit, about 1h 25 min away. There's still lots to do: stroll around Boston Public Garden, buy something for everyone on your list at Faneuil Hall Marketplace, appreciate the extensive heritage of Freedom Trail, and examine the collection at John F. Kennedy Presidential Museum & Library.

To see other places to visit, ratings, where to stay, and more tourist information, read our Boston trip itinerary builder website.

Sofia, Bulgaria to Boston is an approximately 14-hour flight. You'll gain 7 hours traveling from Sofia to Boston due to the time zone difference. Plan for a bit warmer nights when traveling from Sofia in October since evenings lows in Boston dip to 11°C. Finish your sightseeing early on the 7th (Thu) so you can fly to Bar Harbor.

Things to do in Boston

Museums · Historic Sites · Parks · Neighborhoods

Side Trip

Bar Harbor, Mount Desert Island

— 3 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. You'll discover tucked-away gems like Ocean Path and Kayaking & Canoeing. And it doesn't end there: enjoy the sand and surf at Sand Beach, take in the dramatic natural features at Thunder Hole, grab your bike and head to Carriage Roads, and hit the best photo ops around with an inspiring photography tour.

To see traveler tips, ratings, photos, and tourist information, go to the Bar Harbor trip planner.

Fly from Boston to Bar Harbor in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Boston in October, things will get a bit cooler in Bar Harbor: highs are around 17°C and lows about 6°C. Finish up your sightseeing early on the 10th (Sun) so you can go by car to Portland.

Things to do in Bar Harbor

Outdoors · Parks · Tours · Trails

Side Trip

Portland

— 1 night

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.
Kick off your visit on the 11th (Mon): walk around Fort Williams Park and then sample the tasty concoctions at Allagash Brewing Company.

To see more things to do, traveler tips, reviews, and more tourist information, read Portland trip planning website.

You can drive from Bar Harbor to Portland in 3.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. In October, daytime highs in Portland are 19°C, while nighttime lows are 7°C. Wrap up your sightseeing on the 11th (Mon) early enough to drive to North Conway.

Things to do in Portland

Parks · Breweries & Distilleries

Side Trip

North Conway

— 3 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Step off the beaten path and head to Mount Washington Observatory Weather Discovery Center and White Mountain National Forest. Next up on the itinerary: take in the dramatic natural features at Cathedral Ledge, take in the dramatic scenery at Jackson Falls, and cruise along Kancamagus Highway.

For reviews, maps, and other tourist information, read North Conway trip app.

Traveling by car from Portland to North Conway takes 2 hours. Alternatively, you can do a combination of bus and taxi. In October, daytime highs in North Conway are 19°C, while nighttime lows are 8°C. Finish up your sightseeing early on the 14th (Thu) so you can go by car to Lincoln.

Things to do in North Conway

Nature · Parks · Museums · Childrens Museums

Side Trips

Lincoln

— 2 nights
Stretching through the White Mountain National Forest, Lincoln welcomes hikers along the Appalachian Trail.
Kick off your visit on the 15th (Fri): see Off-Road Tours and then take in the dramatic scenery at Sabbaday Falls. Keep things going the next day: immerse yourself in nature at Franconia Notch State Park and then take in the dramatic natural features at The Basin at Franconia Notch State Park.

For more things to do, other places to visit, maps, and tourist information, you can read our Lincoln trip itinerary planning site.

Getting from North Conway to Lincoln by car takes about 1.5 hours. Plan for a bit cooler nights when traveling from North Conway in October since evenings lows in Lincoln dip to 3°C. Finish your sightseeing early on the 16th (Sat) so you can drive to Stowe.

Things to do in Lincoln

Nature · Parks · Tours · Outdoors

Side Trips

Stowe

— 2 nights

The Ski Capital of the East

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
Kick off your visit on the 17th (Sun): trek along Burlington Bike Path and then stroll around Waterfront Park. On the 18th (Mon), you'll have a packed day of sightseeing: take in the awesome beauty at Mount Mansfield State Forest and then cruise along Smugglers Notch State Park.

To find reviews, other places to visit, ratings, and tourist information, use the Stowe trip website.

Traveling by car from Lincoln to Stowe takes 2 hours. Alternatively, you can take a bus; or take a bus. In October, daily temperatures in Stowe can reach 18°C, while at night they dip to 4°C. Cap off your sightseeing on the 18th (Mon) early enough to travel back home.

Things to do in Stowe

Parks · Nature · Outdoors · Trails

Side Trip