Boothbay Harbor, Maine
The Perfect Weekend Getaway
There are places that hold pieces of our hearts—places that shaped us in ways we don’t fully understand until we return. For me, that place is Maine’s rugged, beautiful coast, where I spent twenty magical summers with my grandparents who had retired from New York when I was just two years old.
This year, Steve and I finally made the journey back to Boothbay Harbor after an absence of 34 years. As we planned this long-awaited return, we knew we wanted to stay somewhere special—a place that would capture the essence of coastal Maine while serving as the perfect home base for revisiting all my childhood haunts.
Choosing Topside Inn: Location Meets Character
After researching our options, we decided on Topside Inn for our first visit to this beautifully renovated bed-and-breakfast. What drew us in was its charming character and, crucially, its central location that would allow us to easily explore all the places I’d been longing to revisit: Pemaquid Point, Damariscotta, Muscongus Bay, and Shaw Fishery.
We couldn’t have made a better choice.
Perched overlooking the sea, this enchanting property captures everything magical about coastal Maine hospitality. The inn’s character shines through in every detail: thoughtfully curated artwork featuring sailboats and seascapes, inviting common areas with wicker furnishings and warm lighting, and those picture-perfect views of Boothbay Harbor dotted with sailboats and lobster boats.
First Impressions: Exceptional Service from Day One
As first-time guests, we were immediately struck by the incredible team that made our stay so memorable. A special shout-out to Mary Martin, the general manager, whose attention to detail and warm hospitality made us feel like cherished friends rather than just new visitors. The entire staff—from the talented chef to the friendly hostess—created an atmosphere of effortless elegance and genuine Maine warmth.
The culinary experience exceeded all our expectations. The brunch was incredible, featuring fresh, local ingredients that showcased the best of Maine’s coastal bounty. Evenings at their charming bar were equally delightful, with expertly crafted drinks served in an idyllic setting that perfectly captured the essence of seaside relaxation.
Pemaquid Point
For as long as I can remember, my family has made the pilgrimage to Pemaquid Point in Maine, and every visit reminds me why we keep coming back. There’s something about this place that captures the raw, rugged character of the coast—the kind of beauty that’s unparalleled and impossible to replicate anywhere else.
On this trip, we stumbled upon one of those perfect local moments when a fisherman running a tour in the lighthouse recommended Shaw’s Wharf for lobster. Located just 8 short minutes down the road from Pemaquid Point, it turned out to be exactly what you’d hope for: an authentic fisherman’s wharf experience where the lobster is fresh off the boat and the atmosphere is unpretentious and real. Loved it!!
A Homecoming Within a Homecoming
As soon as we got off the plane, we drove straight to Damariscotta—my grandparents’ hometown for over 20 years and a place that holds even deeper meaning for me. When I was 20 years old, I worked at a restaurant called Schooners Landing, right along the Damariscotta River, which is renowned as the heart of Maine’s oyster industry. This estuary is often called the “Napa Valley of Oysters” and accounts for 80% of all oysters harvested in the state.
I was both thrilled and heartbroken to discover that while Schooners Landing was still operating, the original restaurant had burned down last year. But in true Maine fashion, they’ve adapted beautifully—creating an open boardwalk dining experience with all the fresh seafood I remembered, right there along the river where those famous Damariscotta oysters are harvested. Standing there again, watching the river flow and smelling that distinctive mix of salt air and fresh shellfish, I was transported back to my 20-year-old self, learning the restaurant business in one of Maine’s most spectacular settings.
We spent wonderful hours along Muscongus Bay at a classic lobster dock that epitomizes the authentic Maine experience. This very cool open dock boardwalk operation lets you pick your fresh lobster right from the tanks, and they boil it to perfection while you wait. You can order clams, oysters, whatever you want—it’s all fresh right out of the sea, with the bay and marina right there before you. This is old school Maine at its absolute best, and this particular spot has been operating for over 60 years. Standing on those same weathered boards where I spent countless summer hours as a child, cracking fresh lobster at picnic tables with my family, I was overwhelmed by how perfectly unchanged this magical place remains along the beautiful waters of Muscongus Bay.
Rediscovering Boothbay Harbor’s Timeless Charm
Between our coastal excursions, we loved exploring Boothbay Harbor itself. The walkable downtown still enchants with its collection of charming antique stores and unique shops. I was delighted to find that the original ice cream shop I visited as a young child is still there, along with the beloved taffy and candy store where the fudge is just as irresistible as I remembered.
The seafood scene remains unparalleled—fresh lobster, clams, and oysters that taste like the essence of the Maine coast itself. Every meal was a reminder of why Maine’s culinary traditions have endured for generations.
Evening Magic and Simple Pleasures
Some of our most treasured moments happened right at the inn. Evenings spent playing cornhole on Topside’s grounds while overlooking the sea, watching the harbor lights twinkle to life as dusk settled over the water. Long walks along Boothbay Harbor’s iconic boardwalk, breathing in the salt air and listening to the gentle lapping of waves against the docks.
These are the moments that remind you why certain places become part of your soul.
Your Guide to Boothbay Harbor: Restaurants, Shops & Experiences
For fellow travelers planning their own Boothbay Harbor adventure, here’s a directory of the wonderful businesses that make this coastal gem so special:
Dining Experiences
Kalers Restaurant - Classic Maine seafood at 48 Commercial St
Boothbay Lobster Wharf - Authentic waterfront lobster dining
Thistle Inn Restaurant - Upscale dining with thoughtful food and drink pairings
Ports of Italy - Fine northern Italian cuisine at 47 Commercial St
Ocean Point Kitchen - Classic New England dishes with ocean views in East Boothbay
Robinson’s Wharf - Harbor views and local seafood
Knead & Nosh - NY Style bagels and specialty foods
Maritime Adventures
Eastwind Schooner - Two-hour sailing trips aboard this historic 65-foot schooner, departing from Pier 6 to explore outer islands, lighthouses, and wildlife
Schooner Applejack - Sister ship offering similar magical sailing experiences
Shopping & Specialty Stores
East Boothbay General Store - Perfect for supplies before exploring Ocean Point Loop
Eventide Specialties - Hot meals, sandwiches, and local goods
Various antique stores and boutiques throughout the walkable downtown
The beauty of Boothbay Harbor lies not just in its individual establishments, but in how walkable everything is—you can easily stroll from shops to restaurants to the harbor itself, creating that perfect Maine coastal experience.
A First Stay That Won’t Be Our Last
As we reluctantly packed our bags after four perfect days, I couldn’t help but think about how much I wished I hadn’t waited 34 years to return to Maine—and how grateful I am that we discovered Topside Inn for this special homecoming.
Our first experience at this charming bed-and-breakfast exceeded every expectation. The combination of authentic Maine character, exceptional service, and that perfect location made it possible to reconnect with all the places that had shaped my love for this coast, while creating entirely new memories.
For anyone considering a Maine coast getaway, I cannot recommend Topside Inn highly enough. Whether you’re a first-time visitor like we were or a returning Maine lover, it offers that rare combination of genuine hospitality and a location that puts you at the heart of everything that makes this region magical.
Sometimes the best journeys are the ones that take us home again—to places that shaped us, to memories that sustained us, and to the simple joy of salt air and endless horizons. And sometimes, you need just the right place to call home base while you rediscover all that magic.
Cari Ann Carter is the best-selling author of Are Your Roots Right? Rightsize Your Space. Reclaim Your Life. and a multi-faceted entrepreneur with a passion for intentional living, design, and home.
She leads the Cari Ann Carter Group, bringing over 28 years of experience in real estate, design, build, and renovation, and is the creative voice behind DIY Designer Homestead.
Through Fresh Roots Living, she shares practical ideas for cooking, gardening, entertaining, and creating a home that supports your next chapter.