Log In | Register | Help
Road Trips
2-day Boothbay Harbor and Monhegan Island This roadtrip is a great way to explore a great seaside Maine town and see a coastal island community. Explore Boothbay Harbor during the day, dine at one of the many waterfront restaurants, and then spend the night in town. Get breakfast and then head down to the dock for your second day's adventure: Monhegan Island. You may want to get your ferry choice out to Monhegan squared away once you get into Boothbay Harbor. Also, bring a warm layer for the ferry trip in case the winds pick up.
Day 1: Boothbay Harbor

One of Midcoast's most popular tourist destinations, one can't help but be charmed by this harbor town filled with dining, shopping, and scenic attractions. In between wandering the shops and sampling the many dining offerings, take a stroll over the walking-bridge that spans the harbor or relax with some fresh salt-water taffy on the in-town green.
close
Boothbay Harbor


Staff Photo by John Ewing.
The Heritage from Rockland was one of 14 Windjammers to enter Boothbay Harbor as part of the 37th Annual Windjammer Days celebration in Boothbay Harbor.

Located on the shores of the Midcoast region, Boothbay Harbor is a popular tourist destination. Ocean-view dining opportunities, boutiques (hand-made jewelry, home decor, clothing, gifts, pottery), marinas, art galleries, and souvenir shops line the village streets.

Perhaps the best way to appreciate this seaside town is from the water. Seafaring adventures depart from in-town docks, including windjammer scenic cruises, deep-sea fishing voyages, and whale watching trips.

Visit the Historical Society in Boothbay Harbor and the Museum in Southport to learn about ice cutting and the area's rich ship building culture.

In warm weather, grab scoop of ice cream and relax on one the benches near the water's edge. Did we mention the fresh fudge and salt-water taffy?

There are a number of annual events worth checking out:

The Annual Fisherman's Festival  (late April)
Features Trap hauling, cod fish relay, old - fashioned fish fry, Miss Shrimp Princess Pageant, lobster crate race, and other contests. Location: Main St, Boothbay Harbor. www.boothbayharbor.com.

Annual Windjammer Days Festival (late June)
Full rigged windjammers sail into the harbor. Two fun - filled days of harbor side concerts, fireworks, an antique boat parade, a street parade, games and activities for the children, and plenty of food. Location: Waterfront, Boothbay Harbor. www.boothbayharbor.com.

Annual Harbor Lights Festival  (early December)
Santa and friends arrive by boat, horse drawn wagon rides, craft fair, lighting of the Christmas tree, community caroling and the spectacular Lighted Boat Parade. Times: All day. Location: Downtown Boothbay Harbor. www.boothbayharbor.com.

 

Find local dining review
See more annual events

More about Boothbay Harbor
Day 2: Day trip to Monhegan Island

This year-round island community offers a glimpse into Maine island life. Depending on when your ferry departs back to the mainland, you'll have about three hours to explore the island. The trip to and from the island is an experience in itself. Many tour operators go out of their way to include whale watching on the way home. If you have an extra night, spend the night at one of the island accomodations. Be sure to make reservations.
close
Monhegan Island


Staff photo
A hiker stops to enjoy the view from the characteristically rocky shore of Monhegan Island.
Monhegan Island conjures up so many images that even Mainers who've never been there instantly nod and say "Ah" when you say you're going to the island. They might be thinking of a Jamie Wyeth painting, or a piece by one of the many famous artists who worked or still work on Monhegan. They might be remembering the dispute that lobsterman had over territories with the folks from Friendship. Or they might have heard about the excellent birding that can be done there, and only there, because of its prime spot offshore -- close but not too close.

That might sum up the tenor of the island community. It's close enough so that a year-round population has managed to survive and persevere for at least 100 years. About 75 people live there


Photo By Shawn Patrick Ouellette
Boys take turns jumping into the cool ocean water in the village on Monhegan Island.
year-round. The islanders aren't isolated; they know what's going on, their kids go away to college, they have electricity and telephone lines. But it's not so close that anyone can just decide to live there. It's about 12 miles offshore and winter nights are long and windy. Like many of Maine's island communities, Monhegan struggles to find a balance between the need to attract tourism and the desire to have some privacy.

More about Monhegan Island >

Loading map...

Windjammers in Maine

Built before the age of powerful engines, schooners once relied on the skills of sailors and the winds that weather offered. Around the turn of the century, these vessels transported heavy and valuable cargo between ports and were built for strength and speed.

You can get a taste of what that is like by taking a cruise on one. They offer a chance to try your hand at sailing - if you choose. Or you can sunbathe and enjoy doing nothing. You are bound to make new friends as you cruise Maine's beautiful coastline.

A list of windjammer cruises

American Eagle, 92 feet, 28-passengers, b. 1930, Rockland. (800) 648-4544

Angelique, 95 feet, 31-passengers, b. 1980, Camden. (800) 282-9989.

Annie McGee, b. 1957, Belfast. (888) 818-8234.

Downeast Windjammer Cruises operate several schooners for day sailing trips from Bar Harbor, Bath and Boothbay Harbor. (207) 288-4585 or (207) 288-2373.

Ellida, 10-passengers, b. 1922, Rockland. (888) 807-6921.

Grace Bailey, 80 feet, 29-passengers, b. 1882, Camden. (800) 736-7981.

Goddess of the Sea Cruises, specializing in private day sails and overnight cruising adventures for couples and families! . (207) 649-2628.

Heritage, 94 feet, 30-passengers, b. 1983, Rockland. (800) 648-4544.

Isaac H. Evans, 65 feet, 20-passengers, launched in 1886, Rockland. (877) 238-1325.

J. & E. Riggin, 90 feet, 24-passengers, b. 1927, Rockland. (800) 869-0604.

Kathryn B, 105 feet, 10-passengers, b. 1995, Rockland. (800) 500-6077.

Lewis R. French, 22-passengers, b. 1871, Camden. (800) 469-4635.

Mary Day, 90 feet, 29-passengers, b. 1962, Camden. (800) 992-2218.

Mercantile, 78 feet, 26-passengers, b. 1916, Camden. (800) 736-7981.

Mistress, 60 feet, 6-passengers, b. 1960, Camden. (888) 692-7245.

Nathaniel Bowditch, 82 feet, 24-passengers, b. 1922, Rockland. (800) 288-4098.

Roseway, 137 feet, 36-passengers, b. 1925, Camden. (888) 767-3929.

Stephen Taber, 68 feet, 22-passengers, b. 1871, Rockland. (800) 999-7352.

Timberwind, 70 feet, 20-passengers, b. 1931, Rockport. (800) 759-9250.

Victory Chimes, 132 feet, 40-passengers, b. 1900, Rockland. (800) 745-5651.

Wanderbird, not a windjammer but a 90-foot, 12-passenger converted fishing trawler, Rockland. (866) 732-2473.