Boston to Boothbay

Stretch your legs with a stroll around the boardwalk of Old Orchard Beach. There is a lively lineup of beachfront bars and restaurants where you can snack or drink with your toes in the sand, while the Palace Playland amusement park bustles with carnival vibes in the summertime. Wander out to the Old Orchard Beach fishing pier to drink in the full experience.

Is a donut a destination? It is at The Holy Donut! This hole-in-the-wall bakery with locations on Park Ave and Commercial Street is known for imaginative flavor pairings and homemade dough made from Maine potatoes. The donut menu rotates, but you can choose from up to 20 flavors. Try to visit early—ideally before 1pm—as each location closes when the day’s batch runs out.

The Portland Museum of Art in Congress Square is the heart and soul behind Portland’s funky, artsy atmosphere. Here, at the largest and oldest public art institution in the state of Maine, you’ll find the works of acclaimed painters like Winslow Homer, Andy Warhol, and Claude Monet. Visitors can also indulge in more contemporary exhibitions in the free outdoor sculpture park and surrounding Portland Arts District.
The museum is closed on Mondays and Tuesdays. City development projects may impact parking, so plan your visit ahead.

Before turning down the peninsula to Boothbay Harbor, stop off at Red’s Eats in Wiscassett for an award-winning lobster roll. Locals have voted this more than 80-year-old institution the number one choice in just about every best-of list out there. Not a lobster fan? No problem. There are plenty of other menu items to choose from in the classic fried-food canon. Be prepared to wait a while in summer, but the views overlooking the Sheepscot River will placate your impatient belly.
In spring, Red's is closed on Mondays and Tuesdays. During the summer, the stand is open seven days a week. Check the hours here.

From May to October each year, the Coastal Maine Botanical Gardens put on a show of seasonal blossoms, pollinator exhibits, and some of the most tranquil meditation spaces you’ve ever laid eyes upon. Don’t miss the “Guardians of the Seeds,” a collection of wooden giant trolls who are scattered throughout the landscape to spread the teachings of land stewardship.

Come dinnertime, settle in to the Thistle Inn and Restaurant on Oak Street. This inviting dining room occupies the former quarters of a sea captain, and the period-appropriate vibes are spot-on. They do an elegant citrus salad and a number of ocean-inspired entrées. Dinner is on the pricier side, but they also have an extensive menu of pub fare like flatbreads and sandwiches that won’t break the bank.
The Thistle Inn Restaurant is open 16:00 - 21:00 Tuesday - Saturday. Closed Sundays and Mondays. Reservations are recommended and can be made online.

As far as road trip novelties go, it’s hard to beat a boat-shaped hotel situated right along Boothbay’s scenic harbor. Sixty-four guest rooms are scattered across the wharf, and many have waterfront views. The highlight, of course, is the Tugboat itself. Guests can climb aboard the perfectly preserved wheelhouse, or grab a bite to eat on the roof top deck.