The Getaway
20 Things to Do on Cape Ann, Massachusetts

Cape Ann and its seaside communities make for awesome day trips or longer sun-soaked vacations. This charming area caters to outdoorsy folks excited to go on Atlantic Ocean safaris or hiking and kayaking with endless coastal views, but you can always just loll about eating lobster and building sandcastles on painting-worthy beaches. With its long-held reputation as an artist colony, Rocky Neck draws a more culturally-minded crowd seeking a creative escape. Whatever your mood, Cape Ann is a tonic.


01 Good Harbor Beach

Gloucester, MA, USA August 18 A family enjoys a summer's day at Good Harbor Beach in Gloucester, Massachusetts James Kirkikis/Shutterstock

Arguably the prettiest beach in Gloucester and one of the best on the North Shore, Good Harbor Beach has a large stretch of soft sand and is as family-friendly as it comes. During low tide, a sand bar materializes so beachgoers can walk to Salt Island. When the tide is high, this beach is fantastic for swimming, boogie boarding, or body surfing (actual surfing isn't allowed). A shallow creek offers a lazy river feel, but it's sometimes closed to the public. The seagulls here are brazen, so stay alert and look after your food and belongings.

You can expect restrooms, showers, concession stands, equipment rentals, and cold, refreshing water. During summer, you'll find lifeguards on duty.


02 Wingaersheek Beach

Wingaersheek Beach aerial view in Gloucester, Cape Ann, Massachusetts, MA, USA.

The clear, blue-green waters at Wingaersheek Beach are so inviting. But there's more to look forward to, from big boulders you can climb to tide pools perfect for hunting for crabs and other seaside creatures with kiddos in tow. Look for the "crocodile rock"—you'll know it when you see it, and Annisquam Lighthouse. At high tide during peak season, the beach can feel a little cramped. But when the tide ebbs away, the space opens up, and you can walk quite a distance with the water at waist level. The restrooms and showers here are clean.

You may want to carry a picnic to save on concession costs and take a bag for your trash. Bug spray will come in handy, too. In terms of parking, the fee is steep for non-residents, but free parking is possible in the late afternoons. You can reserve a spot in advance.


03 Singing Beach

Singing Beach at Manchester-by-the-Sea in Massachusetts

Singing Beach is a New England fav over in Manchester by the Sea and gets its name from the dry sand that makes a noticeable noise when you walk on it—it's not quite Donna Summer, but you'll hear a squeak. A 1924 bathhouse includes toilets and changing stalls, and like many of the popular beaches in these parts, lifeguards keep a watchful eye over bathers during peak season. Try and come to the beach early during vacation periods to secure parking.

During the off-peak season, parking isn't an issue even for out-of-towners, and the shore is full of furry four-legged friends living their best lives. Take a relaxing stroll before popping into the Laughing Gull Café.


04 Eastern Point Lighthouse

Eastern Point Lighthouse at Gloucester at Sunset, Massachusetts, USA. The Lighthouse is One of Five iconic lighthouses along the Cape Ann coastline.

The Eastern Point Lighthouse is a historical structure in Gloucester Harbor, America's oldest seaport. The harbor dates all the way back to 1616. The first iteration of the lighthouse was constructed in 1831, but the current tower was built in the late 19th century and is 36 feet tall. It appeared in the movie "The Perfect Storm" (2000). While it's not possible to go inside the lighthouse, you can view it from the Ipswich River Wildlife Sanctuary parking area and jetty. The path here is not suitable for anyone with mobility issues.


05 Thacher Island Twin Lights

Low Tide at Sunrise on Good Harbor Beach, Gloucester, Massachusetts

The thin, twin lighthouses on Thacher Island are together known as Cape Ann Light Station or "Ann's Eyes." They are a National Historic Landmark initially established in 1771 and were the first lighthouses built in North America to signal a dangerous spot rather than a harbor entrance. These twin lights in Rockport are more than three times taller than Eastern Point Lighthouse, and the best place to take pics of them is from the water.

Book a lighthouse cruise with Cape Ann Harbor Tours for an exciting vantage point, or stick to the mainland on Penzance Road. During summer, you can climb the 156 steps to get to the top of one of the twins.


06 Cape Ann Museum

Cape Ann Museum chronicles the culture and maritime history of the region and showcases Cape Ann's longstanding (since the 1700s) arts hub status. You can view works by the esteemed painter Fitz Henry Lane as well as pieces by contemporary creatives and artifacts from local industries. Currently, the museum is open seven days a week from 10 a.m. to 5 p.m. except on Sundays when it's open only in the afternoon.

Admission fees are $15 for adults, $12 for seniors, students, and Cape Ann residents, and free for folks who have library and other passes. Free admission is possible on days like Juneteenth. The museum hosts talks, workshops for beginner and experienced artists alike, and walking tours.


07 Sargent House Museum

Travel back to Georgian times with a visit to the Sargent House Museum in Gloucester. This was where the feminist writer Judith Sargent Murray, who penned "On the Equality of the Sexes" in 1790, lived. So, if you want to learn about inspirational women, you'll learn plenty at this Federalist-era home. The museum also displays original works by the well-known 19th-century portrait painter John Singer Sargent, furniture by Thomas Sheraton, and items of interest from Judith's life.

In addition to house tours, the museum does occasional walking tours of the neighborhood as well as special tours delving into the Murrays' pivotal role in the Universalist church. Sargent House Museum is only open on the weekends in summer and fall.


08 Hammond Castle Museum

John Hays Hammond Jr. was a prolific inventor and mentee of Thomas Edison who built his dream home, a remarkable medieval castle, in the 1920s. The castle contained a laboratory where he could work on his pioneering projects in radio control. It also housed Hammond's personal museum, comprising Roman and Renaissance artifacts. Hammond Castle, with its many stairs, is not wheelchair-friendly, but service dogs are welcome. Choose between self-guided or guided tours, and check out this Gothic venue's calendar for events such as screenings of the movies filmed onsite or yoga sessions on the lawn.


09 Whale Watching Tours

A whale watching cruise boat takes tourists to watch whales off Provincetown, Cape Cod, MA, USA. suefeldberg/ Getty Images

Stellwagen Bank National Marine Sanctuary is famous for its whale-watching opportunities and marine biodiversity. The whale-watching season starts as early as April and ends in October, and you won't go wrong with tour operators like Cape Ann Whale Watch or 7 Seas, who offer multi-hour adventures. Experts such as marine biologists talk you through sightings of humpbacks, minkes, pilot whales, dolphins, seals, or other fascinating animals. If you're prone to motion sickness, take a tablet before you hop aboard, and carry a waterproof jacket or cozy layer to protect against the wind.


10 Kayaking and Paddleboarding

20 Things to Do on Cape Ann, Massachusetts

Cape Ann is a great place to go kayaking or paddleboarding. While sea kayaking is for the more experienced, folks of all ages can try paddleboarding on a whim. Front Beach in Rockport, Lanes Cove on Duley Street, Pavilion Beach in Gloucester, and Corliss Landing are just some of the launch spots in the area.

Cape Ann SUP + Surf rents out equipment, and if you're new to these water sports, you can take lessons or join a tour to build your confidence and gain a deeper understanding of the coastline and Great Salt Marsh.


11 Rocky Neck Art Colony

Rocky Neck is the country's oldest continuously operating artist colony. It's not hard to see why the practice of plein air or painting outdoors was so common here—the light is special, and the landscapes are invigorating. Visit this enclave where Winslow Homer and Edward Hopper once lived and worked, and you'll be treated to live music and monthly exhibitions. Look up the historic art trail map for more info on the studios and galleries in East Gloucester and to see where various artists resided. Different establishments have different opening hours.


12 Gloucester Stage Company

Gloucester Stage is a professional, non-profit theatre company that has been operating since the late 1970s. You can watch classic works and modern plays with high production values in an intimate setting near all the action. Some of the plays go on to become commercial productions in cities like New York and Paris. Ticket prices differ depending on age group, but discounts are available for preview shows, groups of 10 or more, people with a theatre subscription, EBT / WIC Cardholders, and locals attending midweek performances. Arrive early because streetside parking is limited.


13 St. Peter's Fiesta

St Peter's Fiesta is an annual Gloucester celebration on the weekend closest to June 29. It's sponsored by the local Italian American fishing community and draws visitors from out of state. After an open-air mass on Sunday, you can expect a float parade and a blessing of the fleet that ends with fog horns blowing. The festival honors the lives lost at sea while looking to the future with hope. Come for a fun-filled event with carnival rides, yummy food, boat races, and a hilarious Greasy Pole competition where contestants run across a slippery pole to capture a flag.


14 Gloucester Schooner Festival

Keen on making plans for Labor Day weekend? Consider the Gloucester Schooner Festival, a Maritime Gloucester event that has become a tradition over the last few decades. Over four jam-packed days, captains compete, a block party fills the air with laughter and music, food trucks feed boat lovers, and the schooners show off. Tour the decks of these beautiful vessels while they're docked, watch the daytime and twilit parades on the water, or buy a ticket to sail away like Enya, just for a little bit at least.

The best spots to watch the Parade of Sail are Eastern Point, Stacy Boulevard, and Stage Fort Park. Solomon Jacobs Park is optimal for viewing the International Dory Races, and you can view the fireworks from Pavilion Beach, too.


15 Halibut Point State Park

This reservation is ideal for pure R&R in nature. You can chill out with a book and sunbathe or take your canine bestie for a leashed walk through mostly flat wooded trails. The park is dog-friendly throughout the year.

You'll stumble across an old granite quarry filled with water, picnic areas, wildflowers, and gorgeous coastal scenery. While swimming here is unsafe, the cliffs, tidal pools, and Atlantic Ocean views more than make up for the lack of a beach. Bonus points for stroller-friendly hiking and birdwatching, but leave extra shoes and socks in your vehicle in case you step into a muddy puddle.


16 Stage Fort Park

Picturesque Stage Fort Park is part of the Essex National Heritage Area, and its name is a nod to the fishing stages set up by early settlers in 1623 and the garrison present for around 250 years until 1898. Swim at Half Moon Beach, play sand volleyball, take Fido to the dog park, go fishing, enjoy a cookout, or simply sit on a bench and take deep breaths of fresh air. If you've got kiddos with you, there's a playground, and additional sporting facilities include a basketball court, baseball field, and tennis courts.


17 Bearskin Neck

Bearskin Neck will give you all the quaint seaside village vibes you're after. Stop here for a spot of Rockport shopping, to browse through Lauri Kaihlanen or Robert Lerch's galleries, among others, or fill up on fresh, tasty seafood at Roy Moore Lobster Co. Snap selfies with the iconic Motif Number 1, a landmark fishing shack on Bradley Wharf that art history students and enthusiasts should be very familiar with. Parking can be tricky.


18 Maritime Gloucester

Maritime Gloucester's museum and aquarium for kids and young adults offer locals and visitors a deep dive into the area's natural and cultural heritage. Educational programs build marine science and mariner skills, so if you're curious about the fishing business or the world below the waves, you know where to go. Interactive exhibits engage all ages, and staff members are always ready to help and answer questions about the waterfront and beyond. Opening hours are between 10 a.m. and 4 p.m. daily.


19 Essex Shipbuilding Museum

Essex was once a wooden fishing schooner juggernaut, making more of these boats than anywhere else in the nation. History buffs will love the insight into the shipbuilding industry. Visiting hours differ, so check the website for the latest updates and for details about events like hull carving workshops and arts and culture festivals.


20 Main Street Shops in Gloucester

The downtown area in Gloucester, MA, is super walkable, and Main Street is filled with cute boutiques and souvenir shops. Pop into a store like The Brass Monkey for vintage goodies and unique keepsakes and products.

Grab cannolis, cookies, and subs at Virgilio's Bakery, and savor the slower pace of life.


21 The bottom line

USA, Massachusetts, Cape Ann, Essex. Antique signs

Cape Ann comprises Gloucester, Essex, Rockport, and Manchester-by-the-Sea. This area has so much to offer visitors and locals, from its nautical pastimes and professions to an abundance of arts and culture. Go whale watching and be awed by the planet's biggest mammals, search for starfish and clams in salty rock pools or chase lighthouses.

Kick back and relax with theatre productions full of heart and soul, try your hand at plein air painting workshops, or sunbathe and hike in stunning coastal parks. We'd love to know about your favorite Cape Ann spots and experiences, so feel free to share and ask questions. Happy exploring!


Scroll Down

for the Next Article

The Getaway Badge
Sign up to receive insider info and deals that will help you travel smarter.