Boothbay, Damariscotta + Wiscasset

After rainy weather for what feels like weeks, the sun is shining, and I have a case of spring fever. This weekend road trip can’t come fast enough. 


3:30 p.m. @ Fort Edgecomb

Our first stop on the Boothbay peninsula is Fort Edgecomb, located on Davis Island. My husband Rob and I stretch our legs and let the sun warm our faces as we check out this cool, two- story, octagonal blockhouse made entirely of wood. The fort was particularly active during the war of 1812 when it held many British prisoners of war.

4:05 p.m. @ Coastal Maine Botanical Gardens

These are the largest botanical gardens in New England and they’re impressive! We wander around, stopping at the Lerner Garden of the Five Senses and the adorable Children’s Garden and marvel at all the various plant species, amused by names like Helenium “Moerheim Beauty” Sneezeweed and Epimedium “Spine Tingler” Barrenwort.

5:15 p.m. @ Topside Inn

We’re greeted by proprietors Mark Osborn and Buzz Makarewicz, and settle into our light-filled, inviting, third-floor room. The inn is perched atop a hill overlooking Boothbay Harbor, and the view takes my breath away.

6:00 p.m. @ Watershed Tavern

We have plans to meet up with clients from local design and build firm Knickerbocker Group, who quickly become fast friends. The great company, fun stories, cozy atmosphere, and beer brewed on the premises all make for a super evening.

8:15 p.m. @ Boathouse Bistro

There’s no better way to end our first night than some casual fare enjoyed at the bar of this local spot and tapas restaurant in the harbor.


7:30 a.m. @ Topside Inn

Breakfast at the Topside should not be missed. On the menu today: fruit and homemade granola, freshly baked bread with honey walnut butter, and a shrimp, grits, and egg dish that’s simply heaven.

8:00 a.m. @ Linekin Bay Resort 

We feel lucky to get a private tour of this family and sailing resort that is undergoing a revitalization by owners Scott Larson and Steve Malcom. They’re taking great care to update the buildings and grounds while keeping the flavor of the longstanding property intact. The water views from nearly every spot make this a dream for families looking to vacation together.

9:00 a.m. Boothbay Harbor Country Club

Next up: Steve gives us an insider’s view of the new clubhouse at the golf club. Built to impress, there have been no details spared, from a state- of-the-art kitchen to locker rooms that you could live in. Members and golf lovers are in for a treat!

10:00 a.m. @ Trevett Country Store & Mill Cove Lobster Pound

It’s still early, but our busy morning has us hungry. We indulge in our first lobster roll of the season and it tastes like summertime in Maine. Next door we meet Joe Hall of Mill Cove Lobster Pound, who shows us where they process local lobster and seafood, which they sell to venues throughout Maine, New Hampshire, and Vermont.

10:30 a.m. @ Porter Preserve

I am always up for a walk in the woods, and these trails, part of the Boothbay Region Land Trust, are a new favorite of mine. The small area offers various trails that lead right down to the water. It’s both peaceful and stunning.

11:30 a.m. @ downtown Damariscotta

We arrive in this darling town and immediately notice Riverside Butcher, still under construction. Owner August Avantaggio is inside and tells us the shop will feature locally sourced meat. Making our way through town, we visit Sheepscot River Pottery, where we’re wowed by the handcrafted bowls, and stop into Weatherbird to check out a great selection of blue jeans.

12:30 p.m. @ Whaleback Shell Midden

Middens, or shell mounds, are essentially rubbish piles left by prehistoric people. They consist of thousands of oyster shells that have been uncovered and named a historic site. Rob and I try to imagine what it was like for the people living in this very spot so many years ago.

12:30 p.m. @ Newcastle Publick House

Being in oyster territory, we indulge. Lunch is a perfect selection of Damariscotta River oysters: one order plain on the half shell, and one order of the Angry Al’s with bacon, spinach, gorgonzola, and hot sauce.

2:30 p.m. @ East Boothbay 

We stop at the East Boothbay General Store, where you can get gifts, specialty foods, baked goods, and breakfast and lunch. At Ocean Point we walk along the water, feeling the salty air on our faces and taking in the sea view and incredible coastal homes.

4:00 p.m. @ Topside Inn

I’m in need of some rest on the super-comfy bed, but not before grabbing a homemade cookie (a jar of which is always by the front desk).

6:15 p.m. @ Robinson’s Wharf 

Feeling refreshed, we grab a prime seat at this Southport bar for a drink. If only it were a little warmer, the bar windows would open wide and boat watching in the harbor would be in full effect.

8:00 p.m. @ Ports of Italy 

My friend Jonathan Tindal, of Tindal and Callahan Real Estate, gives me an insider’s tip: the best seats in the house are at the bar all the way around the horseshoe. But those seats are taken, so we head to the porch, where we happen to run into some family friends. We catch up and enjoy an amazing dinner of Caesar salad, antipasto, and pasta.


10:30 a.m. @ Boothbay Harbor

We are in need of gifts for our weekend pet sitters, and the newly opened Seawicks Candle shop in town is perfect. Everything smells so good, there are no wrong choices here. Island Teak Company gets my attention, and we take some snapshots of a few furniture pieces that I’ll inquire about later. We then grab a quick snack at Coastal Maine Popcorn and head south.

11:15 a.m. @ Wiscasset 

The town is as cute as its shops. Rock Paper Scissors is a carefully curated space where I ogle a series of bird paintings on wooden blocks. Next door, Birch is filled with beautiful home items. Just down the block, Treats has baked goods that smell out of this world. I grab some bread for later in the week as we decide to make our way to Red’s Eats for a famous lobster roll. Rob gets a spot in line while I pop into Sylvan Gallery and check out some exquisite Maine artwork.

12:10 p.m. @ Red’s Eats 

I’ve heard about this lobster roll since before I moved to Maine. What could be so great to cause lines around the block and epic traffic jams? Luckily, being early in the season, we don’t wait long. And the roll doesn’t disappoint. It is a bit hard to eat because there’s so much lobster packed in there, but we split one and dig in. Toasted bun, butter on the side, I realize this lobster roll is a great metaphor for our weekend: a savory taste of Maine that’s chock-full of goodness. And I can’t wait to go back for more.

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