7 days in Maine, Salem & Sleepy Hollow Itinerary

7 days in Maine, Salem & Sleepy Hollow Itinerary

Created using Inspirock United States itinerary maker

©
Make it your trip
Fly to Boston, Bus to Portland
1
Portland
— 1 night
Drive
2
Salem
— 2 nights
Drive
3
Sleepy Hollow
— 1 night
Drive
4
Bar Harbor, Mount Desert Island
— 2 nights
Fly

S M T W T F S
29
30
31
1
2
3
4
5
6
7
8
9
10
11

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 1st (Wed): learn insider's secrets on The Maine Brew Bus. On your second day here, enjoy the sea views from Portland Head Light, then appreciate the extensive heritage of Marginal Way Walkway, and then kick back and relax at Ogunquit Beach.

To see traveler tips, more things to do, maps, and tourist information, read our Portland holiday maker website.

London, UK to Portland is an approximately 12.5-hour combination of flight and bus. Due to the time zone difference, you'll gain 5 hours traveling from London to Portland. When traveling from London in September, plan for a bit warmer days and about the same nights in Portland: temperatures range from 26°C by day to 13°C at night. Wrap up your sightseeing on the 2nd (Thu) early enough to drive to Salem.

Things to do in Portland

Breweries & Distilleries · Wineries · Historic Sites · Tours

Side Trips

Salem

— 2 nights

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
On the 3rd (Fri), learn insider's secrets on Salem Food Tours and then get interesting insight from Tours. Here are some ideas for day two: get engrossed in the history at Salem Witch Museum, contemplate the long history of The House of the Seven Gables, admire the striking features of Phillips House, then explore the world behind art at Peabody Essex Museum, and finally contemplate in the serene atmosphere at Grace Episcopal Church.

For photos, ratings, where to stay, and other tourist information, go to the Salem day trip planning app.

Getting from Portland to Salem by car takes about 2 hours. Other options: take a bus; or take a train. In September, daytime highs in Salem are 28°C, while nighttime lows are 14°C. Cap off your sightseeing on the 4th (Sat) early enough to travel to Sleepy Hollow.

Things to do in Salem

Tours · Museums · Outdoors · Wildlife

Side Trip

Sleepy Hollow

— 1 night
Sleepy Hollow is a village in the town of Mount Pleasant in Westchester County, New York. To see ratings, reviews, and other tourist information, read our Sleepy Hollow online visit planner.

Traveling by car from Salem to Sleepy Hollow takes 4 hours. In September in Sleepy Hollow, expect temperatures between 29°C during the day and 17°C at night. You'll have a few hours on the 5th (Sun) to wrap things up before traveling to Bar Harbor.

Things to do in Sleepy Hollow

Parks · Historic Sites · Nature · Wildlife

Bar Harbor, Mount Desert Island

— 2 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 6th (Mon): examine the collection at The Seal Cove Auto Museum, take in the spiritual surroundings of St. Saviour's Church :, then get interesting insight from Tours, and finally take your sightseeing to a higher altitude at Cadillac Mountain.

For traveler tips, reviews, maps, and more tourist information, read Bar Harbor attractions site.

You can drive from Sleepy Hollow to Bar Harbor in 7.5 hours. Traveling from Sleepy Hollow in September, things will get little chillier in Bar Harbor: highs are around 24°C and lows about 13°C. Finish your sightseeing early on the 7th (Tue) to allow enough time to travel back home.

Things to do in Bar Harbor

Outdoors · Museums · Tours · Nature

Side Trips

Maine travel guide

4.6
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.