48 Hours in Boothbay, Damariscotta + Wiscasset


When my boyfriend, Chris, and I arrive at the Topside Inn in Boothbay Harbor, we’re greeted with glasses of prosecco and warm homemade cookies. It’s the inn’s first weekend of the season, and owners Mark Osborn and Buzz Makarewicz give us a tour. We’re staying in room eight, which was recently remodeled and is stunning. With a private entrance and a deck overlooking the bay, the room has a spacious soaking tub in the sitting area, a double-vanity bathroom, and a comfy king-size bed.

After we settle in, we make our way to Robinson’s Wharf in Southport for a classic Maine dinner. Chris orders the lobster roll and I spring for the Maine Shore Dinner, which includes clam chowder, corn on the cob, steamers, and a 11⁄4-pound lobster. The atmosphere is laid-back and comfortable, and the food is simple yet delicious. We can’t help but indulge in a warm brownie sundae after our meal.

When we finish eating we head downstairs, where The Grown Ups are playing and locals are dancing. We sit at the bar and order the Thirsty Botanist from Boothbay Craft Brewery.


We consider going out to breakfast but change our minds after we enter the inn’s main building. In addition to the spread of fruit, toast, and yogurt, banana waffles are being made to order.

After we eat, we drive to the Southport General Store for coffee. We continue along Route 27 and loop through Newagen on the southern tip of Southport Island. The sun is shining, and we drive with the windows down as the ocean air fills the car. We make a pit stop near Hendricks Head Beach to take in the gorgeous panorama and the view to Hendricks Head Lighthouse.


It’s our first time in Damariscotta, and as we drive over the bridge leading to the cozy downtown, I notice its charm. We check out a number of shops, my favorites being the Accessories Shop and Sherman’s Maine Coast Book Shop and Cafe. The former has adorable home goods and a wide array of lotions and bath products, and the bookstore has a great selection of titles by national and local authors. I buy a book before we head over to the cafe side and order a cold-brew co ee that really hits the spot.

For lunch we head to King Eider’s Pub, which has a slew of seafood options as well as sandwiches and burgers. Chris orders the smoked salmon BLT, and I get the biggest lobster roll I’ve ever seen. The juicy meat is spilling out of the split-top bun, and the fries are golden and delicious. After lunch I’m craving ice cream, so we drive five minutes away from the downtown area to the highly recommended Round Top Ice Cream Stand. Located in what looks like
an old barn, the simple shop has a huge selection of avors, all homemade. I opt for a small mint chocolate chip cone, which has three heaping scoops, and enjoy it on the sunny back porch.

We head back to Boothbay Harbor to check out a few shops before they close. I’ve been to the town only in the mobbed summer months, and it’s nice exploring the quiet streets in early May. The downtown area is only a two-minute walk from the Topside Inn, which is very convenient. As a dog lover, I’m drawn to Two Salty Dogs, a pet supply store. To my delight, two black labs are lying on the floor, eager to be petted, which I’m all too happy to do.

We also check out the Village Store, which has colorful home goods and kitchenware, and Sweet Bay, where I want to buy everything. The boutique shop has glassware, home decor, and a whole wall of Sea Bags. Then we check out some kitschy gift shops for fun and stop in at Enchantments for some magic.


Since it’s Topside Inn’s opening weekend, the owners are throwing a party for guests and friends. We’re served tasty hors d’oeuvres, and Split Rock Distilling is making blueberry vodka cocktails. After the party, we make the ten-minute walk to the Thistle Inn for dinner. Along the way we stop to walk along the Boothbay Harbor Footbridge, which cuts through the harbor. It’s a beautiful spot to watch the sunset as it reflects across the water.

The Thistle Inn is dark and cozy. Chris orders the baked haddock stu ed with crabmeat, which he enjoys immensely, and I get the seared diver scallops, which are served over lemon risotto and have a sweet-yet-tangy maple-citron glaze. The subtle honey flavor of the Save the Bees cocktail pairs perfectly with the lemon notes in our meals. After dinner we look for a laid-back place to relax before turning in for the night. We stop at Mine Oyster and drink Boothbay Craft Brewery beers on the deck overlooking the water while the sound of the live music inside oats out to us.


We eat another delicious breakfast at the inn, although it’s much different from yesterday’s. The kitchen staff has prepared fish cake Benedict and arugula and pear salad with warm bacon vinaigrette. I’m skeptical of having fish for breakfast, but the meal is exceptional. When we’re done eating, we walk down to Red Cup Coffeehouse for a smooth cup of cold-brew coffee.

We say our goodbyes to Mark and Buzz, then take a drive around Ocean Point Loop in East Boothbay. The homes lining the rocky shores are gorgeous, and the views are even better. The road is narrow and winding, creating the perfect excuse to drive slowly and look out at the water. It’s lightly drizzling, but we still stop the car every five minutes to get out and walk along the rocks.

Before leaving Boothbay Harbor, we have to check out Coastal Maine Botanical Gardens. The newly constructed visitor center and pedestrian bridge are beautiful, and the gardens are a peaceful retreat from the outside world. Not everything is in bloom yet, but the greenery and the bubbling fountains are so relaxing.


There is only one thing on my to-do list when we arrive in Wiscasset, and it’s a must: lunch at Red’s Eats. We join the infamously long line, which isn’t too bad today because of the rain, and wait about 20 minutes to order. Chris, ever health conscious, orders a grilled haddock sandwich, but I go all in and get the fried clam bellies with a side of fries. The clams are huge and hands down the best I’ve ever tasted. I’m on cloud nine.

Happy and full, we totter over to the newly opened Creamed Baking Co. for homemade ice cream. As a lover of Shakespeare and mint chocolate chip, I order the Mint Summer’s Night Dream in a waffle cone, and it is heavenly. Now even more full, we peek into some shops, most of which are still closed for the season. My favorite is Rock Paper Scissors, a fun paper store, where I drool over journals and notepads. We start the drive home to Portland and talk about coming back up as soon as we can.