14 Best Things to Do in Harpswell (Maine)

Located in Maine’s Cumberland County, Harpswell is well known as one of the coast’s most scenic towns and attracts visitors from near and far during the summer vacation season.

The town and surrounding area are an interesting mix of narrow peninsulas and dozens of islands, a few of which are connected by bridges that run between Sebascodegan and Orr’s Island and Harpswell Neck.

The area has always been a popular destination for nature-lovers, artists, photographers, and outdoorsmen, featuring some of the most stunning views and important historic sites in the state.

Below are 15 things to do in and around Harpswell, Maine.

1. Harpswell Hiking Challenge

Thanks to its coastal location, the Harpswell area is home to dozens of islands and hundreds of miles of coastline along Casco Bay and the Atlantic Ocean, making for some of the region’s most rugged and scenic hiking terrain.

For nearly a decade, the town has been hosting a two-day hiking challenge, and the eight trails included change yearly.

The event takes place on the first weekend in June every year, a time when the weather along Maine’s coast is just perfect for being outside.

It’s a great way to burn a few calories, see some fantastic country, and meet some interesting locals.

2. Take a Cruise

Cruises are among the best ways to experience the rugged and beautiful Maine coastline, especially for those with stalwart sea legs who are immune to seasickness.

Operating seasonally from the end of June until the beginning of September, Bailey Island cruises include plenty of amazing natural and historical sites, as well as a running narration describing the things you’re seeing and why they’re significant.

The tours wind their way through the area’s islands and bays, and there’s a two-hour layover at a famous lobster and ale house on the island.

Tours depart from Portland in the morning and Bailey’s Island in the afternoon.

3. Harpswell Historical Society

There’s no better place to start your Harpswell trip than with a stop at the Harpswell Historical Society on Harpswell Neck Road in town.

The society has been around for more than three decades and has been focused on preserving and highlighting the town’s history, economy, and culture ever since.

The sites open to the public include a small museum, Centennial Hall, and communal burial area, with a horse-drawn hearse dating back more than a century.

They offer a variety of unique, instructional and educational activities and programs throughout the year, nearly all of which are open to the public.

4. Old Town Meeting House

Dating back to the mid-18th century, the Old Town Meeting House in Harpswell, was a venue for the town’s residents to meet and discuss the most important issues of the day, and to hold religious services as well.

It’s the oldest building of its kind in the state, and though it won’t take long to see, it’ll give history-minded visitors an interesting glimpse into the past.

The meeting house is free to visit and located in the town’s historic area, so if the weather is nice, consider visiting a few other town attractions on a self-guided walking tour.

5. Cribstone Bridge

Officially listed on the National Register of Historic Places in 1975, the Cribstone Bridge connects nearby Orr’s Island and Bailey’s Island and was initially constructed in the late ’20s.

The bridge’s name comes from the exceptionally massive hunks of Maine granite that were used to anchor its foundation to the harbor floor, which was necessary because the local waters are known for their strong tides and constant waves.

The bridge was considered an architectural marvel for the time, and still offers visitors spectacular views. Both islands mentioned above are worth visits as well, especially for their natural beauty, historical significance, and traditional, coastal charm.

6. Eagle Island

Admiral Robert Peary was a famous explorer who explored the North Pole in the late 1800s, and Eagle Island was once his home.

Now owned by the state and open to visitors, the once private home has been converted into a museum.

The island features a variety of natural trails and beaches as well; it’s possible to get there by ferry from Seaport – this is a particularly good option for vacationers without a car.

For day-trippers, the island is a great place to spend a relaxing afternoon exploring, hiking, swimming, and appreciating the magnificent beauty and historical sites.

7. Halfway Rock Lighthouse

For lighthouse lovers, there’s no better area of the United States to explore than New England.

Dotted with lighthouses of all shapes and sizes, it’s a true mecca for artists, photographers, and all-around lighthouse aficionados.

Located between Capes Elizabeth and Small, Halfway Rock Lighthouse was built in the 1870s. Its name is derived from its equidistant location on a small rocky island between the aforementioned capes.

The lighthouse and island aren’t open to the public, but it’s possible to get close to them on one of the many guided boat tours offered from the nearby cape, many of which are seasonal.

8. Harpswell Community Garden

The town of Harpswell has taken an interesting idea and turned it into a thriving public garden that helps sustain the community and provides all-natural seasonal fruits and vegetables.

Located on Mitchell Field Road just off U.S. Route 123, the garden grounds are owned by the town and are available to locals on a first come first served basis.

It’s a great way to meet other like-minded gardeners. Though as a visitor you may not have time to get your hands into the soil, it’s worth checking out.

If you’ll be around for a while, plots not claimed by locals are available to those residing elsewhere.

9. Cliff Trail

Winding its way through a variety of landscapes, Harpswell’s Cliff Trail is a favorite among locals for its convenience, seclusion, and stunning scenery.

From forests and rocky coastline to islands and panoramic ocean views, the trail packs a lot into a relatively small area.

The trail is only moderately difficult, and though it can get slippery in spots after rain, it’s generally appropriate for most moderately fit hikers, young and old.

The ends of the trail lie at the recycling center and Town Hall, and parking is available at each location. Keep an eye out for the trail markers which are fastened to trees and easy to miss.

10. Black Sheep Wine and Beer Shop

Located on Mountain Road in Harpswell, Black Sheep Wine and Beer Shop is the local go-to destination for those looking for a full selection of tasty adult refreshments.

You won’t find a big selection of stuff from the national mega-breweries and wineries, but you will find a mouth-watering selection of local and regional ones in a variety of styles.

If that’s not enough, they also sell homemade chocolates. If you haven’t tried the combo, you’ll be pleased to know chocolate can match very nicely with dark red wines and stout beers.

Their prices are higher than the local grocery store, but the selection and quality will make those few extra dollars spent well worth it.

11. Ark II Charters

Bailey Island in Harpswell is the launching point for one of the area’s most popular boat tours.

There’s no better way to experience the coast than from a boat. Along the way, guests will get a running historical narration that’s the perfect accompaniment to the natural and historical sites.

The captain and crew have decades of combined experience. Depending on what time of year you visit, you may see seals and other coastal wildlife like dolphins and osprey as well.

The tour boat is a safe and rugged 30-foot Catalina. Though it isn’t cheap, it may be one of the most memorable things you’ll do on the Maine coast. Book in advance if you’ll be visiting during peak season.

12. Reid State Park

In the mid-’40s a well-to-do local man donated the land that’s now Reid State Park to the state; shortly after that, it became Maine’s first saltwater beach park.

A short hike up to Griffith Head gives visitors unobstructed views of the ocean, coastline, and a nearby lighthouse on a harbor island.

The park features wider than normal beaches, which are great places to spend a day frolicking in the sun, sand, and surf.

For beachcombers and shell collectors, the park’s beaches are the perfect places for a long walk when the tide is receding.

There’s no telling what you may find, and the sights will be unforgettable.

13. Popham Beach State Park

Another one of the Harpswell area’s largest beaches is Popham Beach, located in the state park of the same name.

The beach and park are the perfect places for exploring the coast. They are especially appropriate for travelers with children, as they sport more wide open spaces than other local beach parks.

During low tide, it’s possible to walk to a small island offshore; the exposed bars and tidal pools are home to lots of interesting crabs and fish that are big hits with the little ones.

The state park is located in Phippsburg and doesn’t get the crowds that many other beaches do, making it a real gem.

14. Giant’s Stairs Trail

Located in Harpswell, Giant’s Stairs Trail can be difficult to find for locals and visitors alike, and that’s why it’s usually not very crowded.

Much of the trail is gravel and runs along a rocky cliff overlooking the sea. Its stunning views are often highlighted by white, foamy surf and shore birds drifting on the wind. Some of the trail’s most scenic vantage points are near rocky edges, so they’re best left to the sure-footed.

It’s possible to head down to the jagged shoreline, but this is only recommended at low tide, as the area is prone to particularly large and powerful waves.