Photographs + stories by Maine magazine staff:
Jen DeRose, Managing Editor, Old Port magazine

Jen DeRose, Managing Editor, Old Port magazine

It’s Memorial Day weekend, and as my husband, Sam, and I drive through quaint Boothbay, we’re happy to find that the unofficial start to summer seems to come a few weeks later here. We’re happily surprised to find that while all the restaurants and shops are open, the town’s pace remains relaxed and low-key—exactly the way a vacation should be.

Friday

5:04 p.m. @ Bayberry House Bed and Breakfast
As we are checking in to our B&B, innkeeper Chris Swanson comes out to greet us with a hearty hello–and promises an even heartier breakfast tomorrow. The 1886 Victorian he and his wife took over a year ago when they moved here from the U.K. is a comfortable mix of old meets new, with a blend of antique furnishings and modern amenities, such as recently renovated baths. Also, it’s immaculate. At one point in our stay, another guest will say to me, “This is the cleanest place I’ve ever stayed,” and I have to concur.

5:56 p.m. @ Sweet Bay and Tide Pools
A few boutiques are still open, and I’m lured in to Sweet Bay by their Sea Bags display—it’s a definite contender for the largest selection in town. The shop also carries a number of upcycled wares. At Tide Pools, we browse an extensive selection of books, handmade crafts, and vintage clothes, including a funky knit fisherman’s hat that I try on.

6:17 p.m. @ Mine Oyster
Sushi boats festoon the front window, and when we walk in we’re immediately introduced to the sushi chef. We head upstairs where it’s a little warmer, thanks to Mine’s wood-fired oven, and start out with two pint-size Dark ‘n’ Stormys—fitting for the overcast weather. We order half a dozen Cape Blue and Glidden Point oysters, and then dive into steamed lobster while looking out over the harbor. Just as we’re leaving, we hear the band, Mama’s Boomshack, start up.

8:57 p.m. @ Downeast Ice Cream Factory
At this preserved-in-time ice cream parlor, Sam orders scoops of Oreo and cookie dough. I steal a (delicious) taste on our short stroll back to the hotel.

Boothbay Harbor

Saturday

11:01 a.m. @ Oak Street Provisions
This all-purpose shop has shelves and shelves of bottles of wine and bee. It also carries everything you might need for a last-minute cocktail party or to stock up before weekend guests arrive, including fresh-caught fish, homemade lobster cakes, gourmet cheese, four kinds of ginger beer, and The New York Times. Owner Doug Roberts tells us what’s just come in, then whips up two delicious salmon wraps, which we take with us.

11:24 a.m. @ Tidal Transit Kayak Company
I’m used to kayaking in a dirt-covered, creepy-crawly-infested boat that’s been stored under someone’s porch all winter long, so it’s a total treat when Travis Journagan and his crew hook us up with shiny kayaks complete with rudders, spray skirts, and dry bags for our picnic lunch. After giving us a few helpful tips about technique and safety, they send us off with a laminated map and the knowledge that they’ll keep an eye on the radar and call our cell phone if the weather starts to turn. Then we’re taking in Boothbay from a very different view, gliding past lobster boats, shingled houses, and seafood shacks as we paddle along the scalloped shoreline.

2:52 p.m. on Main Street in Damariscotta
An egg cream at Waltz Soda Fountain is a trip back in time and a welcome pick-me-up after our morning on the water. We wander down the historic street, stopping in at S. Fernald’s Country Store, where I ogle wood-and-glass displays of old-fashioned candy, and Seawicks, where I browse a mix of vintage and new coastal-inspired accessories, including their hand-poured candles. At Schooner Landing Restaurant and Marina, we admire the view from the dockside bar and wander into Stars Fine Jewelry, where I contemplate picking up an antique silver baby cup for a unique shower gift.

4:43 p.m. @ Peter and Jean Richards Fine Antiques
A sign outside a red barn tells us to ring the bell, hit the lights, and that someone will walk over from the nearby farmhouse shortly. Once the space is illuminated, my eyes go from the large selection of copper cookware in the front to a pair of baroque gilded mirrors on the wall behind them. Owner Jean Richards arrives and charms us with stories from her former life in New York. She also encourages us to touch pieces’ “It’s not a museum,” she says. When a bentwood Thonet coat rack catches my eye, she pulls it off the wall for me to admire. She tells us about her neighbors who are hosting an art opening next door, but we’re out of time and promise we’ll be back.

5:45 p.m. Down East Gallery Painter
Brad Betts invites us to preview his new gallery before the grand opening next week. He and his wife, who works at Knickerbocker Group, built the farmhouse-inspired space themselves. Two sails hang in the roof beams and filter in light that highlights his maritime paintings, in beautiful shades of saturated blues.

7:32 p.m. Ocean Point
We slowly drive along this three-mile stretch of oceanfront road, a close-knit neighborhood of summer cottages, and wave hello to families out for an evening stroll.

8:25 p.m. @ The Thistle Inn Restaurant
We’re immediately seated in this cozy and romantic restaurant, even though it’s packed. We start out with the Caesar salad. When it arrives, we find that the romaine lettuce has been sliced lengthwise and grilled, the char adding a sweetened smokiness. The dressing and croutons are nestled inside. It’s so good we come very close to ordering a second.

Kayaking in Boothbay Harbor

Sunday

10:06 a.m. @ McKown Street
We squeeze in a little morning shopping, hitting up Goobies, an alternative art space, which has Maine furniture maker Geoffrey Warner’s vintage-looking wood and steel stools in the window and Italian artist Laura Bianchi’s oil on boards displayed on the walls. At Casual Interiors, we spring for a set of made-in-Maine LooHoo felt dryer balls, which are an eco-friendly alternative to traditional dryer sheets. We also pop into Two Salty Dogs to scope out toys for our French bulldog. Finally, we wander down to Lindy Bragg’s clothing boutique, Calypso, where white linen shirts hang in the sun that streams through the shop’s oversize window overlooking the harbor.

11:14 a.m. @ Mainely Scooters
I’m a little nervous to drive a scooter, but the helpful owner provides professional instruction and safety tips. We meander down Route 27 towards Southport, curving around coastal inlets and pausing as a drawbridge opens to let a tall sailboat glide through.

11:48 p.m. @ Oliver’s
I’m excited to try the lobster roll, which we’ve heard is one of the best in Boothbay, but when we walk in, it’s the water view that immediately commands my attention. The 1948 general store was rebuilt in 2012 as a restaurant by the Knickerbocker Group, and features many reclaimed materials, such as wood from bowling alleys that now tops the dining tables.

2:32 p.m. @ Coastal Maine Botanical Gardens
Tulips in shades of coral, creamsicle, and salmon herald our arrival. We wander the grounds, descending toward the mediation garden, an idyllic, contemplative setting tucked in near the seaside. We linger for a few moments, not wanting the trip to end.

4:09 p.m. @ Georgetown Pottery and Portage Company
We almost drive by, but we decide to stop and I’m so glad that we do. We enter Portage first, which features one-of-a-kind local furnishings and art, and then admire the handmade dinnerware, vases, and lamps next door. I’m drawn to the work of artist Elly MacKay, who creates miniature theater scenes of cut paper and then photographs them. We wind up splurging on a colorful print of sailboats. It’s the perfect souvenir from our weekend.