Things to do in Boothbay Harbor, Maine in August

The sea salt and pine tree aroma tickle my senses as we roll by quaint harbors with brightly colored sailboats swaying in the calm waters. The classic coastal cottages decorated with picket fences dot the densely-treed landscape. This is the sweetness of late-summer in Maine when the water is warmest, fresh blueberries are overflowing, and delectable seafood delights are bountiful.

Traveling to coastal Maine is a two-step dance that requires extra effort and may also be the element that makes it so unique. From Boston, I booked the Downeaster Amtrak train from Boston to Freeport, Maine. The business class was clean, empty with comfortable chairs. The scenery quickly changes from urban to suburban and then to dense hardwood forests until it finally opens to coastal-marsh meadows and small-town single stop open-air train stations. The Freeport train station is a vintage open-air stop in the middle of town.

Motoring down Route 1 toward the coast delivers a heavy dose of nostalgia for simpler times, with fields of crops, rickety barns, rusty John Deere tractors, and livestock. Bridges dominate the roadways in this part of the country. You will cross two expansive bridges on your way to Boothbay Harbor.  Sagadahoc Bridge that connects the City of Bath and Woolwich, Maine over the Kennebec River and the shores of Merrymeeting Bay, and the Sheepscot River Bridge, which connects the charming towns of Wiscasset and Edgecomb. When you turn onto Route 27, you know you are getting close. The rivers disappear for a while, and the landscape takes on a small town country flavor with handmade signs for roadside commerce and throwback gas stations.

Southport maine

Upon entering the town of Boothbay, the white picket fences and gray-weathered cedar siding cottages with colorful trim come into view. The tree-lined narrow streets are a confusing network of steep hills and winding drops on a coastal ride by breathtaking scenes of harbors and inlets filled with boats of all sizes, fish markets, ice cream parlors, picturesque shops, luxurious homes, and small cottages.

The area around Boothbay was an early British fishing camp that was purchased by Chris Henry from Chief Robinhood in 1666. After a series of battles and a 40-year abandonment of the settlement, Colonel David Dunbar laid out a new town, which was ultimately renamed Boothbay Harbor in 1730 and continued to develop as a fishing center. Southport was part of Boothbay until it separated on February 12, 1842. Originally called Townshend after Lord Townshend, the name was changed to Southport in 1850.

The sea is the catalyst for survival and adventure. Generations of fishermen make their living fishing lobster, mussels, striper, bluefish, mackerel, and giant bluefin tuna. Anglers pull great catches here, whether it’s on a boat or from shore.


Enchanting antique shops and charming general stores are a commonality for most of the tiny island communities. East Boothbay General Store is an alluring establishment with coffee, smoothies, and tasty sandwiches for all your east Boothbay adventures, and activities such as a stroll along Ocean Point. This scenic walk takes you back to the golden era of summers spent on the coast of Maine. Stately homes and cottages, fabulous ocean views including stunning vistas of the pier, islands, and lighthouses.

We stayed in Southport. The Southport General Store was a frequent stop for supplies, snacks, and even small gifts. The “Possibilities in the Shed” is overflowing with unique coastal treasures, lobster buoys, tin water cans, and old-world trinkets. Our days were launched at the Southport Yacht Club on Cozy Harbor. Our captain would silently motor us out of the secluded harbor into the mid-Maine coast’s brackish estuaries. We filled the day with exploring islands for ideal picnic and lobster bake locations, cliff jumping, tubbing, and casual make-shift sandbar parties with cocktails, waist-deep water chats as the kids splash and chase footballs and each other. It was a fairytale summertime setting.

As the late afternoon approaches, where and what to eat becomes our focus; if an opportunity for a Lobster Bake presents itself, take it! Or stop at Robinsons Wharf Seafood Market for fresh live lobsters to go. They also offer fresh shrimp, scallops, calamari. While you are there, listen to live music (weekends) on their deck. We enjoyed a harborside dinner at the Tugboat Inn Restaurant on their open Top Deck with incredible Boothbay Harbor views. Commuting by boat enhanced our dinner date, and the sherbet-colored sunset was the icing on the cake.

Sunset Boothbay Maine

It’s easy to see why generations of families will forever escape to Maine every summer. Many island cottages and seaside estates are handed down from generation to generation. The intimacy of yesteryear summer amusement is still evident at the Newagen Seaside Inn and Sunset Point. In the cedar-walled game room, old-school bowling lanes, card tables, and foosball tables accompany vintage images of a generation gone by enjoying their summer by the sea. Sunset Point continues to draw small crowds of tourists and locals to enjoy the awe-inspiring colors as the sun sinks into the sea.

vintage photo
maine lighthouse

For centuries, Maine lighthouses stood as beacons in the night on Maine’s rocky coast. They stand to caution sailors and also represent protection for seafarers and their vessels. Since the early 1800s, the Monhegan Island Lighthouse has been an active aid to navigation and a beacon of Maine’s maritime history. In more recent years, it’s become a popular destination for history buffs and those who enjoy picturesque coastal scenery alike.   More lighthouses near Boothbay Harbor:

Water activities are plentiful in the Boothbay Harbor region. Sea Kayaking in a harbor or venture out into the sea and around nearby islands for an adventure. Maybe you seek a wind-powered experience that requires you to use your navigation skills and weather knowledge. You can rent a sailboat or relax and enjoy a daysail or overnight sailing charter (with captain) to see the Boothbay region’s coastline from the sea. Powerboats are plentiful and enable skilled adventurers to navigate waterways far from home.


On the final evening of my trip and after 72 hours of non-stop Maine-flavored activities, my hosts gifted me an authentic taste of Midcoast Maine with an island Lobster Bake. We scouted the location the day before. Logistics, invites, and preparations started early the next morning with multiple boat trips to the island, hours of digging a deep sand-pit, gathering wood, and packing all the ingredients; fresh lobster, mussels, sweet corn, red potatoes. It was a big-delicious effort and I’m sincerely grateful to my hosts for an unforgettable storybook ending to an incredible Maine experience.