We have come to know and love the Casco Bay area of Maine over the last eight years. Alex’s family lives in Harpswell, an hour’s drive (or ferry ride) from Portland. Over a series of Maine posts, I’ll put together an itinerary that starts in Portland and takes you up the coast to Acadia National Park.

Portland & Freeport

A first day itinerary is easy! Fly into Portland, have a meal, explore. Drive to Freeport and go to Maine Beer Company for a flight of the best IPAs that you’ll ever have. Go shop at the L.L. Bean Headquarters.

Brunswick

Brunswick is a classic New England College town, home to Bowdoin College.

Dine outside at Sea Dog Brewing Co.
Shop in the small gift shops.
Grab a flight at Moderation Brewing Company.

Visit Harpswell

Harpswell, south of Brunswick, is a peninsula that connects to three small islands in the Casco Bay. We spend most of our time on Sebascodegan, Orr’s and Bailey Islands. While some of the activities are currently limited due to COVID, I still included links to find updated information as restrictions are eased.
Harpswell was also recently the filming location for the very dark film Blow the Man Down. Our experiences are nothing like the murder mystery that unfolds in the movie (to our knowledge there are no brothels in Harpswell), but it was fun to see our favorite spots on the screen.
Look no further than Alex’s family for art created in Harpswell. Alex’s mom has been painting on the island for many years, and you can see her work at Nancy Grice Studios. His sister Carrie performs as Shrines, and her most recent music video for the song Waves is directed by her husband and filmed in various locations around Harpswell.

Hike Harpswell

The Harpswell Heritage Land Trust maintains a series of trails around the town, perfect for sampling the wide range of Maine landscapes. I’ve listed a few of our favorites below.
A hike on Cliff Trail takes you to rocky cliffs, through a fairy forest, and over mudflats.
Devil’s Back is a densely forested trail that opens to views of the surrounding shoreline.
The Giant’s Stairs take you along the rocky ledges of Bailey Island.

For more details and more hikes, download the map and guide booklet.

*Monotropa uniflora*, Ghost Plant
Cliff Trail Hike

Swim & Play in Harpswell

As I’ve mentioned before, Maine water is cold; even in summer the highest water temps are sub zero. (That’s not true, but that’s my “feels like” temperature assessment when I swim in Maine.) Harpswell offers heaps of options to wade into the cool waters, and the inlets provide calm areas that are perfect for families with young children.
At Mackerel Cove you can swim, picnic, shell, and watch lobster boats in action.
Thomas Point Beach & Campground offers both tent camping and electric sites. You can also pay a day use fee to swim at the small beach. We visited during low tide and the water wasn’t deep enough to swim, but we had fun looking for horseshoe crabs in the mud.
The Islands are full of fun excursions. H2 Outfitters offers kayak tours; seals are a common sight along the shorelines. A ferry tour will take you around the Bay and back to Harpswell or to Portland. The Schooner Alert takes passengers on a sailboat cruise.

Stay & Dine in Harpswell

The islands are filled with house rentals, quiet lodges, and no-frill, clean motels. For a chain hotel, look in nearby Brunswick. If you are looking for an adventurous, rustic stay, The Driftwood Inn has the best cliffside views on Bailey Island in a historic lodge.
The Log Cabin Island Inn is a good option for families with young children; it includes breakfast and has an expansive lawn and swimming pool overlooking the harbor.

In Maine I like to play a game where I count the number of different fruits and vegetables that I eat at restaurants. This is very different from Alex’s game of “how many meals in a row can I eat lobster?” Fresh food, whether from above the ground or below the water, is a highlight of any trip to the Casco Bay area. Our favorites are Cook’s Lobster & Alehouse, Dolphin Restaurant, Salt Cod Cafe, Sundrenched (formerly Morse’s), & Hobrook Wharf.