Boothbay, Wiscasset + Damariscotta

Visitors should explore all of this beautiful region, from Wiscasset and Damariscotta down to Southport, Boothbay Harbor, East Boothbay, and Boothbay proper, to get a true sense for why locals call this home and summer residents have made it their temporary home for generations.

Where we stayed: Russell House Bed and Breakfast

Where we ate:
Robinson’s Wharf
The Thistle Inn
Trevett Country Store
The Carriage House Restaurant

What we did:
Boothbay Region Art Foundation
Ran in Ocean Point
Visited Southport Island
Sherman’s Books and Stationery
Coastal Maine Popcorn Co.
Gleason Fine Art
Boothbay Harbor Country Club
Down East Gallery
Boothbay Railway Village
Jane Dahmen’s Studio
Riverside Butcher Co.


Russell House Bed and Breakfast sits back from the road, white with a red roof, surrounded by a carefully maintained lawn. It reopened in December 2016 after an extensive renovation. Well-known local hotelier Scott Larson and Steve Malcom, owner of construction firm Knickerbocker Group, have teamed up to offer luxury accommodations year- round. Nancy Long, the innkeeper, helps us settle into the first-floor Harlow Suite, with a sitting area and Erin Flett graphics gracing the walls.

Boothbay Region Art Foundation has been promoting visual arts  since 1963, and tonight it is hosting the twelfth annual Maine Photography Show. We’re heading over to see entries by Maine magazine photographer Dave Dostie, who won the Committee Choice Award, and others in our creative circle. When we arrive the crowd has swelled out onto the sidewalk.

Robinson’s Wharf is a local food and drink landmark and one of our favorites. The last time we visited, we came by boat from Yarmouth and tied up with several other boaters to enjoy live music and open-deck seating. Tonight, we listen to a live band on the first floor for a few minutes before heading to the upstairs bar. A local friend has recommended that we have dinner at the Thistle Inn, which is under the new ownership of Anya Heyl and Dick Reid. The 1860s building’s restaurant has dark wood, a couple of fireplaces, and four dining areas. All the rooms are lively with conversation, the dinner courses are delicious, and the staff and owners are personable.


We drive east on Route 96 toward East Boothbay. We ditch the car near Smuggler’s Cove Inn and run a four-mile route south on 96 and Van Horn Road, and then hug the waterfront on Shore Road. This is Ocean Point, and whether you run, walk, or bike, you should plan to enjoy the unobstructed views of Linekin Bay and the dozens of quintessential Maine summer cottages that dot the route. At Grimes Cove, the Boothbay Region Land Trust maintains a short trail that crosses over rocky coastal ledges in front of a gorgeous shingle-style residence, which we later learn was designed by our friend Linda Banks from Falmouth.

We’re back at the Russell House to enjoy the complementary homemade breakfast that Long makes for all of her guests. Today she serves waffles with blueberry compote, cut fruit, yogurt, and granola.


We’ve made a plan to meet Rev. Kit Sherrill and get a tour of the All Saints by-the-Sea chapel in Southport as research for a story Lisa will be writing for the August issue. We drive down a gravel road to a small parking lot before walking a dirt path to the small chapel on the water that holds 100 people. A long dock juts out into the bay for parishioners who choose to arrive by boat. There is a lot of history in this place, and it’s a beautiful spot to enjoy some quietude.

We visit the town landing with a view of Cuckolds Lighthouse and Newagen Seaside Inn across the water. Continuing on, we drive toward Pratt’s Island but take the right to visit Oliver’s at Cozy Harbor. There is no more picturesque spot in the area to enjoy a lobster roll on a warm summer day. From there, we continue north and stop at the Southport General Store and meet co-owner Oliver Cusano. He and his wife, Janet, moved here 13 years ago from San Francisco, and in addition to offering great sandwiches they are known for their well-curated collection of wines. Since we’re close, we visit Hendricks Harbor for a glimpse of the lighthouse.

We’re ready for an espresso and lunch, so we head back to Boothbay Harbor. Our Facebook followers have been encouraging us to stop at Red Cup Coffee House. We get our espresso and enjoy some homey comfort among several groups huddled and talking at small cafe tables. Just up the street is Sherman’s Books and Stationery, and we never pass up a bookstore, especially Sherman’s. I’m pleased to see that they are selling over 20 different magazines from our collective, including guides and back issues. After a quick dash into Coastal Maine Popcorn Co., we visit with Dennis Gleason at his venerable Gleason Fine Art gallery.

We need a lobster roll, one with lobster overflowing from a toasted hot dog bun, and we know that Trevett Country Store is the place to go. The path to Trevett’s takes us past the Coastal Maine Botanical Gardens, past a fish house on the banks of the Back River, and across the bridge to Barters Island. We get our two lobster rolls, the last lobster meat of the day for the store, along with a bag of chips and a root beer. Best lunch ever.

I’ve been wanting to see the new Boothbay Harbor Country Club since it reopened last year. Local philanthropist and businessman Paul Coulombe has spent $50 million to upgrade the club and his attention to every detail is evident throughout the clubhouse. The restaurant, Paul’s Steak House, is open mid-May through mid-October and for members only in July and August. From there, we drive north to visit with Danielle and Brad Betts at the new farmhouse location for their Down East Gallery. They’ve transformed the upstairs, where Brad’s art is already hanging, while they work on the first floor. The barn, with long sweeping views of fields behind, will be renovated for event space. On the return to town, we stop quickly at the Boothbay Railway Village.


Kelly Farrin returned home to Boothbay to reopen the Carriage House Restaurant in 2016 after stints at Azure in Freeport and Melissa Kelly’s Primo in Rockland, and it’s already become a local favorite. We sit upstairs where the decor is casual and nautical, and we enjoy a quenching Gypsy Eyes with Beefeater gin, chartreuse, lime juice, grapefruit juice, orange bitters, simple syrup, curacao, and grilled blood orange. For dinner, we order couscous-stuffed roasted tomato with tapenade and eggplant and tamari-glazed roasted salmon.


We head to the east side of Boothbay Harbor and park at the new Boothbay Harbor Oceanside Golf Resort. Russ Armstrong of Knickerbocker Property Management has been leading a crew around the clock for months to totally renovate the former Rocktide Inn before summer. Boaters will be able to tie up out front, and diners will be able to sit at a long waterfront deck or a covered open-air bar. We leave our car and run back over the footbridge that has connected the two sides of Boothbay Harbor since 1901. Our five-mile route takes us through and out of town and towards the Boothbay Harbor Yacht Club in West Boothbay Harbor. Along the way, we pass Island Teak Company in town, and are reminded we need to come back for summer furniture.

After breakfast at the Russell House, we drive to Linekin Bay Resort for a look at the progress of the renovations. Several common buildings and individual cottages are being renovated at this storied camp that has been accommodating summer guests since 1919. We hope to come back again via boat, as we did last summer.


As we head north, we stop in Newcastle at the home of Jane Dahmen, one of our artists at the Portland Art Gallery. She offers us a tour of her house and art studio, and it does not disappoint. She’s working on a new body of work that will be shown later this summer.

Our final stop is a new butcher shop that we’ve been hearing about for months, the Riverside Butcher Co. in Damariscotta. Owners August and Abby Avantaggio are there with their young daughter. They’ve had a great first year of operation, and we’re pleased to hear that both locals and summer folks have added Riverside to their list of provisioning sources.

As we drive home, we reflect on our trip and make note of the places we will visit when we return this summer.