SATURDAY
9 a.m.

We start our Boothbay adventure (and my husband’s birthday weekend) with a short walk through Ocean Point Preserve, part of the Boothbay Region Land Trust. The milelong Norman Van Horn Trail takes us through a wooded coniferous forest to the eastern shore of Tibbetts Pond and back to our car in the parking lot. Afterward, we stop at Color Field Coffee Company, a self-serve microroastery in East Boothbay run by artist Brad Betts and his son Sam. The roastery’s name refers to an abstract painting style characterized by large swaths of solid color spread across a canvas; examples of color field paintings decorate the tiny but adorable space.

12:30 p.m.

A quick lunch at Footbridge Brewery provides us with some much-needed sustenance to power through the plethora of art galleries and retail shops waiting for us in Boothbay Harbor. We start at Studio 53 Fine Art Gallery and browse works by the gallery’s owners, Heidi Seidelhuber and Terry Seaman, before visiting Gleason Fine Art down the street. At Sweet Bay, I spy miniature framed sea glass art that brings a smile to my face. The store’s collection of Erin Flett bags beckons me, but I resist, buying a candle at Seawicks across the street instead. We peek into Sea Bags and the Footbridge Shop before grabbing a scoop of cookie dough with rainbow sprinkles at Downeast Ice Cream Factory. While eating our treat and enjoying the beautiful weather, we walk across the Boothbay Harbor Footbridge, which was built in 1901 and most recently renovated in spring of last year.

3 p.m.

We take our time browsing the oyster-inspired pottery at Ae Ceramics before heading up the hill to our accommodations at the Topside Inn. We’re greeted with an elderflower-cucumber cocktail, a stuffed goug.re, a warm towel, and sweeping views of the harbor from the highest vantage point in town. Innkeepers Mark Osborn and Buzz Makarewicz and general manager Leanne Cusimano show us around the space: fresh cookies await us in reception, the modest but glamorous BarOne is stocked and ready for the evening, and Virgina Shaffer of Lady Oyster is busy setting up an oyster and wine-tasting experience in the dining area. We have the luxury of staying in the Carriage House Suite, but Leanne tells us the newly renovated king room in the main house (originally built by Captain Cyrus McKown in 1865) is the place to be. Thought to be McKown’s primary bedroom, the second-floor corner room features scenic views of the harbor, a tiled and marble wet bathroom with a soaking tub and walk-in shower, dual vanities, dramatic lighting, and a navy blue paneled wall with a contemporary coastal chic aesthetic designed by the innkeepers themselves.

7 p.m.

Outside the inn, we spy a sculpture by William Royall, part of the Boothbay Region Sculpture Trail. Dinner is at the Thistle Inn Restaurant—one of several local restaurants recommended by the Topside team—where we enjoy French onion soup, steak tips, and a slice of carrot (birthday!) cake.

SUNDAY
9:30 a.m.

The Topside Inn is known for its curated sweet or savory breakfast buffet, and we’re excited to try it out. Today, we’re greeted with a savory spread: two kinds of seasonal frittata, a peach and tomato caprese salad, fresh blueberry muffins, yogurt and granola, and plenty of coffee and OJ. Afterward, we walk down the hill to Pier 8, where we board the 47-foot Novelty, also known as the Squirrel Island mailboat, for a one-hour narrated tour around the bay with Balmy Days Cruises.

noon

On our way out of town, we have three stops to make. Up first, the Coastal Maine Botanical Gardens. I’ve only ever visited during Gardens Aglow, when the entire area is lit up for the winter holidays, so it’s exciting to see everything in bloom. The weather is spectacular, and we enjoy meandering through the gardens while laughing at the silly plant names we come across.

2:30 p.m.

Upon leaving the gardens, we stop at Knickerbocker Group’s Boothbay office and meet Danielle Betts, president of the organization and partner of the aforementioned artist, Brad Betts. Danielle gives us a tour of Juniper, a 500-square-foot prefab pod designed and built by skilled craftspeople at the group’s in-house manufacturing facility. The energy-efficient, move-in-ready pod (which won a 2024 AIA Design Award) features a modern aesthetic with a kitchen, bathroom, living room, and bedroom. We say goodbye to Danielle and drive down the street to meet Brad at Down East Gallery, the antique farmhouse and barn where he showcases his own art alongside works from other Maine artists. Betts’s oil paintings primarily depict summer days in Maine—blue skies, billowing sails, and shimmering seas—which are the perfect summation of my weekend in the Boothbay region.