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Friday
Beach picnics and an intimate dinner

Start your weekend off catching the afternoon sun at Pine Point Beach in Scarborough once most beach-goers have retreated for the day. Bring a blanket, and don’t forget to stop at On the Vine Marketplace, located on Route 1 at Dunstan Crossing, for some light provisions. In addition to having a butchery, bakery, deli, and produce, they also carry prepared foods, cheeses, local beer, and wine—all the makings of a beach picnic! Before heading back to the hotel, make a pit stop at Dunstan Tap and Table. With a large outdoor space, the restaurant offers lawn games in the summer and firepits to warm you in the winter.

Check in to your home for the weekend at Inn by the Sea in Cape Elizabeth for a moment of relaxation before dinner. Aside from being a stone’s throw from Crescent Beach State Park, Inn by the Sea casts the ultimate seaside-chic vibes with private balconies, porthole windows, splashes of nautical red and turquoise throughout, and a classic shingle siding.

There’s no need to venture far for dinner when you can enjoy an intimate meal at the hotel’s restaurant, Sea Glass. Be sure to make a reservation, and enjoy some seafood favorites like the New England clam chowder and Faroe Islands salmon, or stick with go-to comfort foods like French onion soup and a roasted half-chicken.

Saturday
Lighthouses, whoopie pies, and local shops

Start your morning off from the comfort of your private balcony with a cup of coffee or tea and a spectacular ocean view. For breakfast, head down the street to C Salt Gourmet Market, where you can grab a bagel with lox or a breakfast sandwich to go, along with a few locally made gifts for your friends back home. Since you’re visiting the Cape Elizabeth area, you’re likely planning to seek out some lighthouses, so start at Two Lights State Park and grab a spot on the rocks for the best view of Cape Elizabeth Light. You may be surprised to find only one lighthouse there: the other, western light of the once twin lighthouses—the first twin lights on the coast of Maine—ceased operation in 1924 and is now a private home. If you’re up for another one, the famous Portland Head Light, Maine’s oldest lighthouse, is just a ten-minute drive away.

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Now that you’ve checked off one quintessential Maine item on your list, it’s time for another: whoopie pies. Stop by Cape Whoopies in South Portland and enjoy a whoopie pie now or grab a couple to go. The chocolate cake with vanilla cream is a classic, but if you prefer red velvet cake or even funfetti, you’ve come to the right place.

Once you’ve had your sugar fix, walk it off in nearby Knightville. The South Portland neighborhood is known for its locally owned shops, and antique lovers will adore Bonny Read, a vintage store filled with a curated selection of midcentury and antique home decor and jewelry. If you’re a foodie, check out Solo Cucina Market for some fresh pasta or locally raised meat. Pair it with a bottle of wine, and you’ll thank yourself later. Before you head back to the hotel, grab a couple local craft beers to go from Foulmouthed Brewing. If you like classic beer styles, go for Beer (yes, that’s its name), but if you’re up for something different, try the Yuzu Kosho Gose—a little sour, a little spicy, and very refreshing.

Before dinner, grab a cocktail on the deck at Saltwater Grille in South Portland for the best view of the sunset over Portland Harbor. A short drive away, Bug Light is also a great place to watch boats coming and going from the working waterfront.

Located on the water at Spring Point Marina in South Portland, North 43 Bistro offers the ultimate indoor or outdoor experience, with a cozy dining room and bar and two levels of outdoor decks. The menu is ever-changing and offers a variety of options, such as miso-glazed shrimp, chicken marsala, strip steak, and beef or veggie burgers. With a cocktail menu that changes as well, there are plenty of reasons to keep coming back. A Razzy Rita on the deck on a hot summer day? Count us in.

Sunday
Exploring waters and wildlife

Soak up the last of the ocean views at Inn by the Sea while enjoying a hearty breakfast at Sea Glass. Don’t forget to make a reservation! We recommend the eggs Benedict, blueberry pancakes, or classic Route 77: eggs, bacon or sausage, herbed potatoes, and toast.

The Cliff Walk on Prouts Neck in Scarborough is a special and unique place to experience Maine’s rocky coast on a clear day. Art lovers can also catch a glimpse into history when passing by the Winslow Homer Studio, where Homer lived and drew inspiration from for some of his most famous paintings. There’s no parking on-site at the Cliff Walk, but if you’re up for a drink at the Black Point Inn, customers there can park for free. Otherwise, Ferry Beach offers plenty of parking for those who don’t mind the extra walk for breathtaking views.

For lunch, stop by Scarborough’s first and only brewery, Nonesuch River Brewing. The big, red barn-style building is hard to miss, so stop in for maple-chili wings and a cold IPA 2.0 to wash it down. Before heading out of town, take a stroll down the Eastern Trail. The 60-plus-mile route runs from Kittery to South Portland, and if you join near Black Point Road in Scarborough, you can walk right through the largest saltwater marsh in the state. It’s one of the top places to birdwatch in Maine, so you’ll want to bring your camera and try to grab a shot of a great blue heron or snowy egret to take with you as a memento.

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