Maine is my summer place. I grew up going there with my family, to the region southwest of Portland, where my grandparents owned a three-season lakeside cottage. More recently, I’ve ventured beyond the lakes, especially to Maine’s storied Atlantic coast. My rambles have taken me to quiet coves and packed seafood shacks, to art galleries and antique malls. Here’s how I would plan the perfect summer getaway.
Pick your home base
Ogunquit
Vibes: This breezy, classic Maine beach town draws crowds of families and older couples all summer long.
Do: Walk the Marginal Way, a thumbnail of a coastal trail that offers cliff-top views of the Atlantic, jaw-dropping seaside homes and the sprawling beach below.
Eat: Cornerstone, which serves excellent pizzas and craft beer in unpretentious downtown digs, attracts as many locals as travelers.
Stay: Anchorage by the Sea is an Ogunquit mainstay thanks to its prime seaside location and its emphasis on Maine-style comforts like fire pits, cozy Adirondack chairs on the lawn and a great on-site seafood restaurant.
Portland
Vibes: Maine’s largest city manages to feel urbane and lively without ever seeming like it’s overdressed or in a rush. The cobblestone streets of its downtown area are lined with award-winning restaurants and fun shops.
Do: Get out on the water. Sailing and boat trips of all kinds, from fishing excursions to leisurely sunset cruises, leave daily from the piers near the old port.
Eat: Central Provisions serves elegantly prepared new American fare in a moody brick-walled space downtown.
Stay: The Press Hotel, with is black-and-white, typography-inspired design, pays homage to the newspaper that once called the building home.
Damariscotta
Vibes: Riverside Damariscotta has all the beauty and none of the crowds of its seaside neighbors. It’s also a great base for roadtripping up and down the coast.
Do: Hop on board with Damariscotta River Cruises to learn about oyster harvesting in the region. You might even catch sight of the harbor seals that swim up river to find dinner.
Eat: At Bred in the Bone, a Mediterranean-style menu is made exclusively with locally grown ingredients.
Stay: The town is devoid of hotels, so vacation rentals are the way to go in and around Damariscotta.
Booking accommodations
Searching for a summer stay in Maine? Book early. That’s especially true if you’re looking to stay along the coast. Expect limited availability and sky-high prices at the last minute, though you can still score some better rates if you’re staying inland and daytripping to the coast.
Scheduling your days
Once you’ve chosen your base, plan to spend one or two days there exploring and the rest of your time daytripping. Each of the cities mentioned above unlocks a host of possible excursions, and they’re also easily reachable from each other by car.
For Ogunquit, head to York with its famous lighthouse at Cape Neddick or go north to Kennebunkport, arguably the most famous Maine beach town.
For Portland, take a culinary deep dive or visit to one of the city’s museums. (The Children’s Museum and Theater of Maine gets high marks from my four-year-old niece.) Portland also makes a great short trip by itself. If you’re staying in Portland, it’s an easy drive to the rollicking Old Orchard Beach, with its old-fashioned pier and throwback roller coaster. Seaside walks on Cape Elizabeth are also an easy drive from town – just expect to spend some time hunting for streetside parking once you arrive. And the shopping outlets in Freeport were designed for rainy days.
If you’re staying in or around Damariscotta, a drive to the towns of Rockland and Camden are a must, as is a trip to Boothbay Harbor, which still feels like a small fishing village.
Because it’s Maine, I’d be remiss if I didn’t mention Acadia National Park, which is a 2.5-hour drive north of Damariscotta, the northernmost base city mentioned above. You can see the park’s highlights in one day by sticking to the main Park Loop Road, but you won’t see everything unless you allocate more time. If you’re choosing this excursion, get an early start to avoid crowds and summer heat.
Plan your meals
Portland’s food scene is a delight, whether you’re on the hunt for burgers, pho, or izakaya. Take the time to plan out your meals here and make reservations, as popular and well-reviewed restaurants may not be able to accommodate walk-ins.
Outside of Portland, lobster rolls, fresh oysters and fried seafood like shrimp and scallops dominate the culinary landscape. Expect waits in July and August at places like Barnacle Billy’s, a classic New England seafood joint with a back patio that overlooks Ogunquit’s Perkins Cove. Stay long enough to see the opening of the cove’s 80-year-old manual footbridge, maybe while sipping the restaurant’s signature rum punch. You’ll find similar salty dog vibes up and down the coast at places like Cape Neddick Lobster Pound (York), Lobster Shack (Ogunquit) and Schooner Landing (Damariscotta).
If you’re ready to shuck your own oysters or grill codfish steaks on the back patio of your vacation rental, Fisherman’s Catch (Damariscotta) is a charming shop that has fresh seafood but also nicely curated accompaniments like marinades and wines. In Portland, Harbor Fish Market in the old port is the place for oysters and heaps of local charm.
Getting there and getting around
For travelers who are coming from outside the region, most Maine trips start at Boston’s Logan Airport or at Portland International Jetport. Flights into Boston are more frequent and thus generally less expensive, but you can find lower fares into Portland by booking six to eight weeks ahead.
You will need a car to do any meaningful exploring outside of Portland. However, the town itself is walkable and it’s feasible to visit for a weekend relying only on your feet and rideshare apps.
Keep planning your trip to Maine:
Plan a Maine tour with these beautiful road trips
Revel in the beauty of the Pine Tree State at Maine's best state parks
Enjoy the best of Maine's coast at these amazing beaches
