Friday Evening: A rocky coast drive and a harborside meal

Following East Boothbay’s peninsula to Ocean Point and looping back on Shore Road will start your trip with stunning, unobstructed views of Maine’s coast. Along the narrow drive you can catch views of not one but three lighthouses: Burnt Island Light, Ram Island Ledge Light, and Cuckolds Light.

On the way through East Boothbay, stop for provisions at East Boothbay General Store. The store sells an eclectic mix of snacks, wine, beer, and Maine gifts, and is best known for its breakfast and lunch menu, including an over-stuffed ham and hard salami sandwich called Vinnie the Shipbuilder and a lobster roll (available seasonally).

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Continuing around Ocean Point Road will lead you to the Boothbay Harbor Oceanside Golf Resort. Located at the water’s edge, the resort offers fantastic harbor views, water-front docking and shuttle services, and a beautiful oceanside restaurant, Coastal Prime. For warmer days Coastal Prime has some of the best al fresco dining in Boothbay. Enjoy any of the fresh seafood dishes (including a special sushi menu) while taking in a stunning harbor-side sunset. If you visit during the off-season, cozy up by the indoor fireplace and enjoy a candlelit dinner.

Saturday Morning: Across the footbridge breakfast and shopping

The Boothbay Harbor Oceanside Golf Resort is just steps away from the Boothbay Harbor Footbridge, a wooden pedestrian bridge that connects the east and west sides of the harbor. It is not only an iconic attraction; it also makes for easy access to the downtown shops and restaurants.

On the other side of the footbridge is Harborside Tavern, with a menu featuring simple classics that are sure to please the whole family. From the two eggs with sausage, potatoes, and toast to its famous and flawless cinnamon bun, breakfast at Harborside Tavern is a great way to start the day on this side of the harbor.

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Walk up the hill, and you’ll find yourself in the heart of downtown Boothbay Harbor, where boutiques, coffee shops, and bars are around every corner. Sherman’s Maine Coast Books is a two-story paradise for any bibliophile or lover of Maine-themed tchotchkes. Directly across the street is Jansons Clothing Store, which carries classic nautical brands such as Sperry, Helly Hansen, Grundens, and Xtratuf. Sea Bags, another iconic coastal brand, is just a few doors down. The walls of the store are lined with totes made in Maine from recycled sailcloth. The designs range from a sand-dollar wine bag to a blue and white number-12 tote for fans of New England Patriot Tom Brady.

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The large white and red storefronts of The Smiling Cow and Gimbel and Sons Country Store on Commercial Street are packed with jams and jellies, marinades and sauces, clothing, greeting cards, Maine saltwater taffy, groceries, and cigars. If you don’t get your fill of treats and eats there, keep following the road up to Eventide Specialties, where you’ll find a wide selection of fine olive oils, balsamic vinegars, and wines from all around the world. Unabashedly preppy and proud is the aesthetic at Maine and Ivy, which curates a collection of clothing, shoes, and bags inspired by the coast.

Saturday Afternoon: The scene in Southport

South of Boothbay Harbor and connected by a bridge is the slightly quieter town of Southport. If you continue on Hendricks Hill Road, you’ll run into Southport General Store. Similar to its East Boothbay counterpart, the store offers household basics, a grocery section, and a menu of classic breakfast and lunch options. Stop in and stock up before exploring Southport.

Continue past the general store and follow Beach Road to reach Hendricks Head Beach. You can scramble along the rocky shoreline to catch a glimpse of Hendricks Head Light or climb to the top of the tiny Kitten Island during low tide. Nearby is the Hendricks Head Preserve, with one of the Boothbay Region Land Trust’s signature trails, an easy half-mile hike through pine forests just steps away from the sandy beach.

Take a slight detour onto Cozy Harbor Road to discover the Cozy Harbor fishing village along the Sheepscot River. Home to the Southport Yacht Club, this hamlet has no shortage of coastal charm and scenery.

Just past a sign for Pig Cove Road on Route 238, a small drive will lead you to the eastern shore of Southport, where a weather-worn, shingle-style chapel sits under a canopy of trees. All Saints by-the-Sea holds services from mid-June to mid-September, but visitors can stop by anytime to beachcomb during low tide or walk out on the pier to view Squirrel Island across the water.

Saturday Evening: Dinner and drinks at two local favorites

A Southport mainstay for decades, Robinson’s Wharf is beloved by locals and visitors. The restaurant sits on a cove just beyond the bridge that connects the island to the mainland. It’s all about seafood at this local institution, where the lobster is caught and picked daily.

For a nightcap back in Boothbay Harbor, visit The Thistle Inn’s cozy and welcoming pub. In warmer months, a large patio is lit up with twinkle lights. Whether you’re from here or away, you will feel at home at this local favorite.

Sunday Morning: A cafe and a cruise

Few places in the area rival the homey charm of Mama D’s Cafe. Pick a favorite coffee mug from the self-serve coffee bar to fill with organic, fair trade coffee from Wicked Joe. Belly up to one of the two bars or enjoy a view of the harbor from the charming front porch.

Getting out on the water is a mandatory part of any visit to the Boothbay region. Balmy Days Cruises out of Boothbay Harbor offers a variety of excursions, including sailing trips, guided mackerel fishing, and harbor tours. The one-hour sightseeing trip aboard the Novelty, the Squirrel Island mail boat, features views of the Maine State Aquarium, Burnt Island Light, and often a harbor seal or two.

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Just outside of downtown, the Boothbay Railway Village offers family fun, or make an appointment at Cove by Knickerbocker Group for some serious home inspiration.

Sunday Afternoon: Tapas and trails

The Boathouse Bistro Tapas Bar and Restaurant serves a large selection of tapas and local seafood dishes. In the summer the restaurant opens two wraparound porches that look over the harbor. Check the restaurant’s Facebook page to plan a visit for trivia or karaoke night.

On your way out of Boothbay, visit the Ovens Mouth Preserve. The 146-acre preserve of the Boothbay Region Land Trust is actually two peninsulas that are connected by a footbridge. The east side of the preserve includes an easy one-mile loop trail along the Back River with plenty of opportunities to capture photographic mementos of your trip to the Boothbay peninsula.