48 Hours in Boothbay + Damariscotta

Boothbay and Damariscotta are the perfect waterside towns to explore during summer days and weekend getaways.

Walking the waterfront

When my mom and I pull up to The Thistle Inn, we are welcomed by its quaint and charming exterior. We are cheerfully greeted by Mary Lou Koskela, the host at the inn, and she leads us to our room, the Victory Chimes suite. It’s a beautiful suite on the first floor with a bed fit for a king. Shortly after arriving, my mom and I go to the Boathouse Bistro Tapas Bar and Restaurant for a quick appetizer of lobster bisque and Manchurian cauliflower. Afterward, we explore the surrounding waterfront and make our way down to the pier. The sun is setting, and the air has a nip to it as we walk on the footbridge across the harbor to finish our dinner at Coastal Prime, the restaurant at the Boothbay Harbor Oceanside Golf Resort. My mom and I enjoy a perfectly fried plate of calamari while she sips a glass of malbec.

Historic lands and farm stands

We wake up early to start our day in Damariscotta. We head to Crissy’s Breakfast and Coffee Bar for a breakfast of homemade corned beef hash and wild Maine blueberry pancakes. Every bite is delicious, and it is the perfect start to our busy day. We stroll the early-morning streets of Damariscotta before making our way to the Whaleback Shell Midden State Historic Site. When we arrive, the sun is shining brightly, and the air is starting to warm up. The winding path to the shell midden is lined with illustrated poems and endless apple trees. We find a swinging bench overlooking the Damariscotta River and enjoy the spot for a moment before continuing to the shell midden—a mound of shells and other cultural materials such as broken ceramic pots, which were discarded by Native Americans more than a thousand years ago.

On our way back toward downtown Damariscotta, we see Clark Farms and stop to browse. The quintessential Maine roadside store is stocked with fresh herbs, vegetables, fruits, jams, and pumpkins. My mom finds a jar of pumpkin butter, and I buy a jar of dilly beans.

Downtown Damariscotta

Our first stop downtown is The Shady Lady, a perfectly eclectic antiques shop filled with chandeliers and other lights. We are enticed by the wood carvings in the windows at The Wooden Alchemy of Rob Jones and stop in to see Jones’s intricate artwork. We then make our way to Sherman’s Maine Coast Bookshop and browse the aisles for a while before deciding that it’s time to eat.

At S. Fernald’s Country Store, we order sandwiches and grab a seat by a window. My mom chooses the Colossus, with smoked turkey and ham, and I order the Hysterium, a grilled sandwich with avocado, provolone cheese, and sprouts. Both sandwiches are perfectly toasted and the fillings evenly proportioned. After lunch, we explore Main Street a bit further and stumble upon the Chapman-Hall House, a historic house built in 1754. Going inside the museum is like stepping into a time capsule, and each room is decorated with period clothing, household items, and furniture. The home, which is the oldest standing building in the town and one of the oldest in the state, is managed by the Lincoln County Historical Association, which offers tours in the summer.

Eating the night away

After exploring downtown all morning, my mom and I are ready for a break. We take some time to unwind in our room at the inn before dinner. After resting for a bit, we head to dinner at The Thistle Inn Restaurant. We start the meal with an appetizer of Maine crab cakes, which are cooked and seasoned perfectly. For our entrees, my mom orders the blackened Atlantic salmon, and I order the baked haddock. Both plates are as beautiful as they are delicious, and we struggle to save room for dessert. To finish the meal, we share a crisp, golden crème brûlée—it’s the perfect way to end a dinner fit for royalty.

Boothbay’s best

My mom and I are up early to begin our last day exploring. Our breakfast at Harborside Tavern in Boothbay Harbor consists of scrambled eggs, bacon, and blueberry-stuffed French toast. After breakfast we drive to Ocean Point Preserve and enjoy one of the final days of summer. We spend time combing the beach for shells, rocks, and ocean treasures. Much to my delight, I discover the largest piece of pink sea glass that I have ever seen.

We check out of the inn and make our way to the Coastal Maine Botanical Gardens. The facility is gargantuan but welcoming, and we follow the signs to the gardens. We walk through the butterfly garden and chat with the knowledgeable staff about the winged insects and their lifespans. Afterward, we slowly meander the trails, stopping to marvel at the intricate and well-cared-for gardens and various flowers. There’s so much to see that we can’t finish it in one day, but we make a promise to each other that we will be back soon to see the rest. We leave the gardens to begin the journey home—but not without stopping for lunch first.

On our way back through Boothbay, my mom and I stop for lunch at Karen’s Hideaway. It’s a hidden gem inside a trailer on the side of the road. We order a lobster roll, pineapple coleslaw, and mozzarella sticks to share. The food is fresh, delicious, and filling. We finish our lunch as we say goodbye to a wonderful weekend filled with adventure and head home.