1. Where to Stay
Stroll through an acre of lush gardens at the Charles Hovey House (from $135), a bed-and-breakfast in downtown Gloucester. This Victorian home is adorned with plenty of antiques, but it stands out for its colorful, tidy rooms and a veranda that overlooks the harbor, an ideal viewing spot for fireworks over Labor Day weekend.
Make yourself at home in the lofty penthouse suite at Rocky Neck Accommodations (from $140), a short walk away from galleries, shops, and restaurants in the historic Rocky Neck Art Colony. The apartment’s simple interior is reminiscent of a beach cottage, complete with a private deck overlooking the water, and a kitchenette where you can prepare freshly caught lobsters purchased from Turner’s Seafood.
Let the sounds of the ocean lull you to sleep at the Bass Rocks Ocean Inn (from $269), named after the low rumbling of the Atlantic waves just across the street. The property features two newer buildings, the Oceanfront and Seaside Houses, but you’ll find the most charm in the Stacy House (from $379), a turn-of-the-century home where the original Colonial Revival details have been preserved, but the second-floor suites feature modern amenities such as Jacuzzi tubs.
2. Where to Eat
Join the locals who flock to the Causeway (78 Essex Ave.; 978-281-5256) for fresh Italian seafood dishes in a no-frills setting. There’s almost always a wait for a table, so make a stop at the liquor store next door for beer to drink with fried clams and oysters (from $11), or a fruity red to go with a heaping platter of seafood marinara ($20). Either way, plan on sharing a bowl of the hearty fish chowder ($7) that’s loaded with hunks of flaky haddock.
Find a stylish dining experience at Alchemy, a quirky bistro filled with mismatched furniture that serves handcrafted cocktails ($12) and offers the best wine list in town. The menu features a mix of global influences, so in the same meal you could have a watermelon-and-red-cress salad ($12), octopus fricassee ($9), and pork belly tacos ($12).
Dine with fellow art lovers at the Rudder on Rocky Neck, where ivy and white string lights illuminate the simple dining room, but the real ambiance is out on the deck, situated in a quaint cove lined with private docks. Expertly prepared seafood is the reason to come here, whether you have it in a risotto ($28) or just make a meal out of standout appetizers like fish tacos ($14), Moroccan-spiced pulled pork and scallops ($15), and Portuguese-style clams ($17).
3. What to Do
Hop on the harbor water shuttle ($10 for a day pass) to Rocky Neck Art Colony, one of the country’s oldest communities for working artists. Once you arrive, you can visit more than twenty galleries and studios to see new work on display; be sure to stop into the cultural center, located in a tiny, steepled church on Wonson Street, where you can see contemporary photography as well as paintings. Afterward, pick up a map of the Rocky Neck Historic Art Trail, and embark on a walking tour of twelve historic sites, including scenes made famous in the work of Edward Hopper and Winslow Homer.
Skip the popular whale-watching excursions and head for the Cape Ann Museum ($10 admission) to see the Folly Cove Designers collection, a series of mid-century linoleum block prints made with exquisite detail by a local community of mostly female textile designers. Also on display are early Winslow Homer sketches drawn during one of two of his extended stays in Gloucester, and the largest collection of seascapes by Fitz Henry Lane, a nineteenth-century Cape Ann artist who focused on the beauty and toil of the working seaport.
Head northwest on Route 127A for a counterclockwise driving tour of Cape Ann that showcases the dramatic ocean views that have inspired poets and artists for more than a hundred years. Stop at Halibut Point State Park ($2 parking fee), the northeastern point of Cape Ann that juts into the icy Atlantic, where you can walk quiet trails, dip your toes into tide pools, and have a picnic on a rocky ledge overlooking the water.
4. Insider’s Tip
Arrive on Thursday and start your weekend early with lobster rolls for less than $10 at the Seaport Grille. Expect a wait, as locals make this dinner special a weekly ritual, but the yeasty rolls from nearby Virgilio’s Italian Bakery teeming with generous portions of sweet claw and tail meat are worth it.
5. Oddball Day
Take some time to explore Gloucester’s nonartistic offerings, starting with fresh scones from Alexandra’s Bread (265 Main St.; 978-281-3064), where you should arrive early before baked goods start to sell out. Then head southwest for three miles on Route 127 to Hammond Castle Museum ($10), originally built by early-twentieth-century inventor John Hays Hammond Jr. as a present for his wife. Said to be haunted, the castle draws paranormal enthusiasts, but you’re here to freely roam the manicured grounds and enormous halls embellished with oddities and medieval artifacts. Grab lunch back in town at bustling Destino’s and order the linguiça sandwich ($6.50), a soft Italian roll stuffed with the spicy Portuguese sausage that shows up on menus all across town as a testament to Gloucester’s Portuguese working-class heritage. On the side you’ll get a cup of soup (often fish chowder) and access to the “salad” bar, usually a selection of creamy coleslaw and cool macaroni and potato salads (choose the latter). After lunch, head to Main Street to explore Mystery Train Records, which claims to have the largest selection of vinyl in New England. Next, take a right onto Duncan and circle around the Harbor Loop, searching for placards designating stops on the Gloucester Haborwalk, a well-curated, outdoor walking museum with more than 40 points of historical interest relating to T.S. Eliot, Joan of Arc, and more. Turn left onto Rogers Street and continue to follow the self-guided tour until you reach Cape Ann Brewing Co. Settle in with a pint of hoppy Fisherman’s Ale and traditional pub food on the sun-drenched back porch, where the blond wooden benches evoke German beer halls, and watch the bustling harbor grow quiet in the evening hours.
Edward Hopper All Around Gloucester lets you view the 100-plus images Edward Hopper painted of the area alongside the real locations.
Gloucester’s official tourism website has information on local beaches and lots more.