Cape Cod gets all the attention in the summer months. It also gets the traffic, and the crowds. But it certainly doesn’t have the lock on New England picturesque, even as far as capes go. About 40 miles north of Boston and made up of four towns — Rockport, Essex, Manchester-by-the-Sea, and Gloucester, which is actually a city — Cape Ann is 58 square miles of beaches, boats, and fried seafood, all easily accessible by car or, even better, commuter rail. Here’s everything you need to know to plan an easy, satisfying getaway that’s less than an hour from the city and blissfully Sagamore-free.
> WHERE TO PLAY
MANCHESTER-BY-THE-SEA is the quietest and most conspicuously suburban of the Cape Ann towns, with a compact center located about a half mile from Singing Beach, whose sand really does seem to “sing” in the wind (978-526-7276). Parking at the beach is for residents only Friday through Sunday in the summer, with limited availability for nonresidents on weekdays. Luckily, the walk from the commuter rail station (or your parking spot downtown) is a pleasant one and the reward — Singing Beach’s typically uncrowded, sandy sprawl in the shadow of wooded, rocky cliffs — is worth the effort. Once you’ve arrived, the Laughing Gull, formerly the Singing Beach Canteen, is on hand to provide sandwiches, iced coffee, and extra SPF if you run out (978-526-4103). Let a cone from Captain Dusty’s (978-526-1663) or a glass of wine on the patio at The Landing at 7 Central, if that’s more your speed. be your motivation for the walk back to the car (978-526-7494; thelandingat7central.com).
In GLOUCESTER, away from the slightly gritty downtown — it is a city, after all — there are a variety of beautiful sandy shores to choose from, including East Gloucester’s bustling Good Harbor Beach and the kid-friendly still waters of Wingaersheek Beach with the Annisquam lighthouse in view in the distance. Though the fishing industry has been consolidated in recent years, the town remains deeply connected to, and proud of, its seafaring roots — it’s America’s oldest fishing port — and, should it rain, there’s plenty to see indoors. Downtown, the Cape Ann Museum — reopening August 19 after renovations — houses centuries’ worth of fishing- and boating-related artifacts, while the man at the wheel statue overlooking Gloucester Harbor pays tribute to the thousands of fishermen who over the years went off to sea and never came home, including the real-life men immortalized in the Hollywood blockbuster The Perfect Storm (978-283-0455; capeannmuseum.org). Ten minutes east of downtown, the artists and other residents of Rocky Neck populate 100-year-old cottage homes packed into a tightknit, walkable village with ample water views. Here, studios run by artists like clothing designer Sigrid Olsen, sculptor Walker Hancock, and playwright Israel Horovitz commingle with galleries and dockside restaurants along the charmed Rocky Neck Avenue (rockyneckartcolony.org).
ROCKPORT’S Millbrook Meadow (millbrookmeadow.org), an expansive, grassy knoll prime for picnicking or book reading, regularly hosts community festivals and music events (rockportartfestivals.com), while the Headlands, often called “the overlook capital of Cape Ann” is a locals’ favorite, with postcard views of the village, the harbor, Motif No. 1 (Rockport’s oft-painted landmark), and Straitsmouth Island Light, plus plenty of birds. Find the entrance to the Headlands where Atlantic Avenue meets Bearskin Neck. The renowned Shalin Liu Performance Center, whose main stage overlooks the harbor, offers a full schedule of music, theater, and film year-round, including the Rockport Jazz Festival starting August 13 (978-546-7391; rockportmusic.org).
> WHERE TO STAY
As the two busiest communities, Rockport and Gloucester have the most to offer in terms of things to see, eat, buy, and do, and all roads lead here besides. As such, they make the most sense to serve as home base from which to explore the rest of Cape Ann. (That said, if you’re looking for an overnight, the waterfront Essex River House Motel, under new ownership, is a clean, quiet, centrally located option with no minimum stay policy, rare around these parts (978-768-6800; essexriverhousemotel.com).
In GLOUCESTER, the sprawling Bass Rocks Ocean Inn offers unencumbered views of the Atlantic (and the occasional seal), as well as a pool, roof deck, and fire pit. Borrow a bike from the hotel to ride to any number of Gloucester’s wide, sandy beaches or cruise around the coastline (888-802-7666; bassrocksoceaninn.com). For artists and writers, or those who just like being around them, Rocky Neck Accommodations comprises 11 rooms in two buildings in the center of the colorful artists’ enclave of Rocky Neck, all of which come with water views, original exposed beams, and modern conveniences (978-804-0562; rockyneckaccommodations.com).
ROCKPORT, a town that embodies “cute,” is home to many historic bed and breakfasts, each as quaint and cozy as the next. A few standouts, however, include the Emerson Inn by the Sea, a classic New England Victorian-era inn, complete with oceanfront veranda. It’s a 2-mile walk to the shops and restaurants of Main Street and Bearskin Neck, but the view and nighttime ocean breeze — nature’s white noise machine — more than make up for the mildly extra effort (978-546-6321; emersoninnbythesea.com). The 1790 Colonial Tuck Inn is an intimate B&B that’s a shorter stroll from the center of town and as warm and welcoming as staying with friends. Breakfast-time bonus: Owner Scott Wood, who runs the place with his wife, Liz, is known for his homemade bread (978-546-7260; tuckinn.com).
> WHERE TO EAT
It’s hard to go anywhere in Cape Ann without running into a clam, and a perfectly turned out one at that, but ESSEX takes the prize whether you like yours fried, steamed, stuffed, on the half shell, in chowder, or all of the above. You can’t go wrong with Essex landmark Woodman’s, which has been serving up classic New England fish shack fare to crowds for 100 years (978-768-6057; woodmans.com), or the more upscale Shea’s Riverside Restaurant & Bar across the street, where boaters end the day anchored to the bar in front of a bowl of steamers and a few pints of Ipswich ale (978-768-6931; sheasriversideessex.com). The new C.K. Pearl, run by the Sheas’ son Patrick just next door, leans toward a more modern take on the local haul, bolstered by a varied menu of burgers, charcuterie, and creative cocktails and sangria. There’s plenty of waterfront seating with a killer Essex River view and a fun, young crowd (978-890-7378; ckpearl.com).
ROCKPORT is the place for just-caught lobster; it’s on the menu everywhere, from the casual counter service and seat-yourself back deck at Bearskin Neck shack Roy Moore Lobster Co. (978-546-6696) and local favorite Flav’s Red Skiff (978-546-7647) to the decidedly fancier My Place by the Sea, on the tip of Bearskin Neck (978-546-9667; myplacebythesea.com). For the lobster mother lode, don’t miss Lobsterfest, held on August 9 this year (rockportrotary.org). Crustacean-free kids and other culinary landlubbers love Top Dog, a hot dog and clam shop also on Bearskin Neck (978-546-0006; topdogrockport.com). Follow any and all of the above with house-made chocolates and saltwater taffy from Tuck’s Candy Factory (978-546-2840; tuckscandyfactory.com) or an espresso with a harbor view at Bean & Leaf Cafe (978-546-7500; beanandleafcafe.net). A select number of restaurants in Rockport, a dry town until 2005, now serve alcohol, and this year the Emerson Inn by the Sea opened the town’s first full-service bar. Certain rules still apply, though: No booze without food. Try to consider it less a mandate than practical life advice.
For a more varied culinary experience, the choice is GLOUCESTER, which has in the past few years experienced a restaurant renaissance that thrives on a sea-to-table philosophy. Market, founded by two Chez Panisse alums in a former Annisquam fish market, serves up a daily changing menu of local bounty — Atlantic-caught bluefin tuna, butter lettuce from nearby Apple Street Farm in Essex, owned by L’Espalier chef Frank McClelland — in the quaint setting of the aptly named Lobster Cove (978-282-0700; themarketrestaurant.com). Downtown Gloucester holds Short & Main — this sister restaurant to Market features oysters and wood-fired pizza (978-281-0044; shortandmain.com); a Cape Ann outpost of Boston hotspot Franklin Cafe (978-283-7888; franklincafe.com); and worth-the-wait breakfast joint Sugar Magnolia’s — that’s Sugar Mags to the locals (978-281-5310; sugarmags.com). At Latitude 43, fresh-caught local fish stars in everything from chowders and entrees to sushi in a cozy warm space decorated with subtle maritime flair, while its bar, Minglewood Tavern, hosts live music and an occasionally, let’s say, “spirited” crowd (978-281-0223; latfortythree.com; minglewoodtavern.com). A good portion of the 20 beers on draft comes courtesy of the Cape Ann Brewing Co. just down the street (978-282-7399; capeannbrewing.com).
> WHERE TO SHOP
Pro tip: The new Cape Ann Cultural Districts app, a free download that includes recommendations for where to go and what to do around the cape’s four communities, features a navigation tool to help get from one destination to the next. Parking in ROCKPORT is traditionally tricky — few spots, by design. For those arriving by commuter rail, there is a new walking pathway to the downtown area. Drivers, meanwhile, can opt to park in a free lot and take a quick and regular $1 shuttle located on Route 127 just before entering downtown (townofrockport.com). The town, itself fairly Rockwellian in feeling, has a long history as an art colony, and galleries abound. Cape Ann Artisans offers a downloadable guide at capeannartisans.com — if you’ve got your eye on a particular gallery, call ahead to be sure they’re open. The Mosher Gallery, run by husband-and-wife artist team Donald and Christine Mosher, specializes in New England vistas and scenic oils (978-546-3666; moshergallery.com), while Windemere Art & Antiques, owned by former Cars drummer David Robinson, is more eclectic, with an assortment of stained glass, drawings, and paintings from local and nonlocal artists, along with vintage jewelry and tableware (978-546-3513). On Bearskin Neck, the John Caggiano Gallery is run by the renowned landscape artist (978-546-2414; johncaggiano.com). Elsewhere in town, find creative gifts and decorative housewares at The Galleree (978-546-9007); cookbooks, gourmet sundries, and kitchen accessories at Lula’s Pantry (978-546-0010; lulaspantry.com); home accessories at Milk & Honey (978-546-6546; milkandhoneyhome.co); and, well, books at Toad Hall Bookstore, which is notable not just for its comprehensive selection but also for giving 100 percent of its profits to environmental projects (978-546-7323; toadhallbooks.org).
MANCHESTER-BY-THE-SEA, though not a shopping destination, is not without ways to part with your cash: After a trip to the beach, stop in to Gladstone for a tightly curated selection of contemporary and antique jewelry (978-704-9410; gladstonejewelry.com) and, next door, family-owned furniture boutique Cargo Unlimited (978-526-7869; cargounlimited.com). Across the way, the charming Manchester By the Book is overstuffed, in the best way, with used art books, novels, and kids’ series, including many first editions and leather-bound rare finds (978-525-2929; manchesterbythebook.com). Bring an iced coffee from the Grove and prepare to spend some time (978-704-9388; thegrovema.com).
Meanwhile, don’t leave GLOUCESTER without a trip to new, used, and rare vinyl dealer Mystery Train Records, where members of the friendly staff will also recommend their favorite local bands (978-281-8911; mysterytrainrecords.com). Along the water at Stage Fort Park, at the site of Gloucester’s first settlers, the expansive Cape Ann Farmers’ Market features more than 70 local food and craft vendors, along with cooking demos and live music, every Thursday from 3 until 6:30 p.m. (capeannfarmersmarket.org).
New this year, the 1-mile Historic Essex Walking Tour provides an overview of the shipping town of ESSEX, settled in 1634, as well as such landmarks as the Essex Shipbuilding Museum, Cogswell’s Grant, the Cox Reservation, and many of the antiques shops along Main Street. Pick up tour info and download a map at essexwalkingtour.com or find brochures posted around town. Or simply spend the day — or two; there is that much to find here — treasure hunting on your own. The Scrapbook deals in early historical and decorative prints and maps from the 1550s to the 1920s (978-768-7404; allprintsandmaps.com). For a more curated selection of goods, Andrew Spindler uses his Sotheby’s background to inform the often-quirky, always-pristine assortment of furniture, prints, and objects at his Main Street gallery (978-768-6045; spindlerantiques.com). David Neligan Antiques — it’s the one with the stone lions flanking the entrance — specializes in restoring and reselling 17th- and 18th-century furniture and decorative arts from Europe (978-768-3910; davidneliganantiques.com). And at Main Street Antiques, owner Robert Coviello has been dealing in everything old for 33 years, and now offers four floors of antique and refurbished American and European furniture, glassware, lamps, and much more (978-768-7039). As Coviello likes to say, “If we don’t have it, you don’t need it!” — a phrase, it turns out, that may very well sum up the whole of Cape Ann itself.
Correction: Because of an editing error, the website for the store Milk & Honey in Rockport was incorrect in a earlier version of this story. It is milkandhoneyhome.co.