Discover The Best Things to Do in Cape Ann 2025

Cape Ann is a rocky peninsula North of Boston along the coastline and includes the cities and towns of Essex, Gloucester, Ipswich, Manchester-by-the-Sea, and Rockport. Whether you’re interested in exploring a specific town or city or want to experience all of Cape Ann, let us help you find the best things to do in Cape Ann.

Ocean Oasis and Outdoor Thrills in Gloucester

The coastline along Cape Ann is an escape where you can find outdoor activities for any type of interest. Whichever season you decide to visit, Cape Ann has got you covered for apple picking, cruises, and some classic beach time. 

Russell Orchards in Ipswich, MA

Russell Orchards in Ipswich, MA, is a perfect fall and summer getaway. During the fall season, you can pick your own apples. During the summer months, you can pick your own blueberries, blackberries, cherries, raspberries, currants, and jostaberries. Plus, enjoy the delicious taste of cider donuts, fruit pies, and hard ciders, all made on the farm. 

Essex River Cruises in Essex, MA

Hop aboard an Essex River Cruise and take in the natural beauty of scenic salt marshes and unique wildlife. From May until October, the Essex River Cruises and Charters set sail seven days a week with a United States Coast Guard-certified public cruise and experienced Captain and Crew. We recommend making a reservation before you make the trip.  

Singing Beach in Manchester-by-the-Sea, MA

Did you know that Singing Beach will make unusual sounds when you walk on the sand? Check it out and see for yourself. The half-mile-wide, crescent-shaped beach is known for its soft sand and clear blue waters. You can park at the beach lot from June 21 until Labor Day. From October 15 to April 15 there is non-resident parking in designated areas. 

Find more places for outdoor adventure North of Boston.

Step Back in Time With Museums in Cape Ann

Cape Ann played an integral part in shipbuilding and fishing within the global economy. Discover more about Cape Ann’s legacy, and how Gloucester is known as one of the oldest seaports in the country. 

Cape Ann Museum

Uncover the rich artistic, cultural, political, and economic traditions of the area at the Cape Ann Museum, open from Wednesday to Sunday, 10 am to 5 pm. Founded in 1876, the museum features four historic structures, including a sea captain’s house, the original Gloucester town green, modern galleries, art studio spaces, children’s spaces, and an extensive library. Explore rotating exhibits such as the collection of work by native son and marine artist Fitz Henry Lane. 

Castle Hill on the Crane Estate in Ipswich

Live a lavish lifestyle without breaking the bank by visiting Castle Hill on the Crane Estate. This seaside estate was built in the 1880s by J.B. Brown, who made the former Indigenous land into a gentleman’s farm. Then, Chicago Industrialist Richard Tellar Crane Jr. and his wife Florence Higinbotham Crane transformed the farm into one of America’s great Country Place Era estates. You can tour the estate house, gardens, and landscape to discover summertime in Ipswich 1929 for the Crane family. The grounds are open daily from 9 am to 5 pm from February through October, while in November through January, they are open from 9 am to 4 pm. 

Manchester-by-the-Sea Museum

Unveil Manchester-by-the-Sea’s fascinating past at the Manchester-by-the-Sea Museum. This museum, originally a home, was the first house in Massachusetts to be built for a single woman named Abigail Hooper. Within this space, you’ll find restored period rooms, paintings, sculptures by master artists, an impressive collection of MBTS-made furniture, and an outdoor Salt Cod Fish Yard. 

Find more places to get in touch with history North of Boston.

Delicious Bites in Cape Ann that’ll Tame Your Appetite

All that walking around can make anyone hungry! But don’t fret. There is something for everybody throughout Cape Ann from seafood to pub food, and more.   

Woodman’s of Essex

Enjoy delicious Yankee fare at Woodman’s, where the fried clam was invented over 100 years ago. You can gather with friends and family and order hearty portions of award-winning seafood for everyone to enjoy. Plus, the restaurant is open year-round, meaning you can try some clam chowder, fresh lobster, and locally harvested steamed clams at any time of year! 

Ipswich Ale Brewery

For those who are 21 and over, Ipswich Ale Brewery offers great-tasting ales and lagers. You can enjoy 15 tap lines of beer and a diverse selection of food that features brewpub cuisine to New American. The brewery is only minutes away from the Commuter Rail and is close to downtown shops, galleries, and museums. 

The Gloucester House

Eat some world-renowned lobster and yummy calamari at The Gloucester House. During the month of May, you can enjoy their outside takeout window, the Blue Collar Lobster, known for its fast-casual dining experience. From October through May, the restaurant has inside offerings where you can try locally sourced seafood. 

Find more places to enjoy delicious food North of Boston

Get Lost in the Art in Cape Ann

Cape Ann is thriving with artistry all around. Take a break from museum sightseeing or outdoor adventures and enjoy the elegance of music and art all around Cape Ann.

Cape Ann Symphony in Manchester-by-the-Sea

Listen to the harmonious sounds of a live orchestra with the Cape Ann Symphony. This professional orchestra has performances throughout Cape Ann including Ipswich High School and Manchester Essex RHS. Explore upcoming performances and make sure to buy tickets ahead of time, as the Cape Ann Symphony sells out fast! 

Art Galleries in Ipswich

Ipswich is blooming with art galleries throughout the area. If you’re interested in discovering more about art in Ipswich, here are some galleries to check out. 

Hall-Haskell House

The Hall-Haskell House is a part of the Ipswich Visitor Center with the left side of the house operating as a gallery showcasing local and regional artists, which change weekly from June to October. The house is open seven days a week from Memorial Day until Indigenous People’s Day. Hours vary with Monday open from 11 am to 3 pm and Tuesday through Sunday open from 10 am to 4 pm.  

Ipswich Museum

At the Ipswich Museum, you’ll find the largest collection of oil paintings, watercolors, photographs, ink wash drawings, wood block prints, and plaster casts by Arthur Wesley Dow. Dow was born in Ipswich (1857-1922) and created art that was reflective of his time there. 

Find out more about art all around North of Boston. 

Plus, if you come to visit Cape Ann in June or October, you might be able to catch the Cape Ann Artisans Tour, a self-guided tour where you can explore professional artists showcase their work throughout the Cape Ann area. 

Shop till You Drop with these Cape Ann Goldmines

It wouldn’t be a successful trip without a little shopping trip. As Cape Ann has many stores, you are sure to find something special for a loved one or even yourself. 

Shopping in Essex

Essex is home to shops where you are sure to find one-of-a-kind gifts. Shop American artisan gifts like tote bags, mugs, shirts, and sweatshirts at Sea Meadow Gifts. Andrew Spindler Antiques and Design and David Neglian Antiques are great places to find antique furniture. For high-quality antique prints, head to The Scrapbook. 

Shopping in Gloucester 

Gloucester offers several stores, including Mark Adrian Shoes, Second Glance Thrift Store, and the Bookstore of Gloucester. Downtown Gloucester, Gloucester Crossing, and the Harborwalk are just some of the neighborhoods where you can walk down the street and find shops that hold unique treasures.

Shopping in Manchester-by-the-Sea

While Manchester-by-the-Sea might be a small town, you can still find shops during your journey there or after a long day at the beach. Find some seaside souvenirs at 4 Beach Gifts and Goodies or try on fashionable shoes and clothing at boutique consignment and estate sales shop Madam Had’em. You can even find beautiful jewelry at Mahri. 

Shopping in Rockport

In Rockport, Bearskin Neck is the place to be with locally-owned shops, galleries, and restaurants, along tiny narrow streets. The allure of these stores is that there are no brand-named stores to be found. That means you’ll only see speciality gifts that are irreplaceable. 

Find more shopping opportunities North of Boston.

Restful Hideaways to Catch Some ZZZs 

You could spend a whole weekend or a couple of summer days in the Cape Ann area. The rocky peninsula offers several relaxing and chic accommodations for any kind of traveler. Whether you’d like to stay in Essex, Gloucester, Ipswich, Manchester-by-the-Sea, or Rockport, you’ll find plenty of hotels or inns. 

Find more places to stay North of Boston.

Cape Ann is booming with culture, ocean life, and earth-shattering food. See for yourself when you make the trip to Cape Ann. During your journey, make sure you stop in Gloucester, Rockport, and other fun areas North of Boston.