If you are in need of a summer vacation on the Massachusetts coast, but can’t seem to fit it into your schedule, consider visiting Boston’s North Shore over a long weekend. There are so many things to do and see that even a quick trip will rejuvenate you and make you feel like you were able to “get away from it all.” Here are some ideas to help you get the most out of your Cape Ann vacation getaway.
1. Go to the Beach
Nothing says “summer vacation” like a day at the beach. The North Shore has a wide array of world-class beaches, like Good Harbor Beach, Wingaersheek Beach, Singing Beach and Crane Beach, just to name a few. Spend the whole day, or if you want to get more out of your long weekend, spend just a half a day. Pro tip: As this is one of the area’s most popular summer activities, we recommend timing your beach visit either earlier in the day to get in before the crowds, or later in the afternoon (after 3pm) as the bulk of the visitors start leaving.
2. Go on a Whale Watch
Whale-watches are a fantastic way to spend a day out on the water and get a little marine education in at the same time. Gloucester is considered one of the best ports for whale watch trips, as it is located in between two important whale feeding areas, Stellwagen Bank and Jeffrey’s Ledge. For a great day at sea, the crew at 7 Seas Whale Watch are knowledgable and entertaining and they guarantee whale sightings on their excursions. There are both morning and afternoon whale watch options, which mean you still have plenty of time in the day to see other sights, dine in a local restaurant, or go to the beach.
3. Explore the Village of Rockport
We recommend dedicating one of your long weekend days to exploring Rockport. From Dock Square to the tip of Bearskin Neck, the vast collection of boutiques, art galleries, ice cream shops, restaurants and seafood shacks ensures something for everyone. Spend a few hours browsing on your own, or catch a free Walking Tour, given by The Rockport Cultural District. Tours start daily in summer in Dock Square. For the music aficionados: make sure you catch a performance at the incredible Shalin Liu Performance Center, located on Main Street. Search our Rockport accomodations.
4. Find a Local Festival, Block Party, or Concert
There are amazing events taking place on the North Shore every weekend in the summer. Upcoming events for 2025 include Gloucester’s Block Parties (July & August), Newburyport’s Yankee Homecoming (Late July/ Early August), Beverly Homecoming (Late July/ Early August), Festival by the Sea in Manchester-by-the-Sea (late July), the Gloucester Blues Festival (August), the Gloucester Waterfront Festival (August), the Gloucester Schooner Festival, (September) and Trails & Sails, taking place in locations throughout Essex County (September). Find these and other local events here.
5. Watch the Boats Go By
When you need to take a break from touring around, sit back and relax while you watch Cape Ann’s sailboats, fishing boats, and schooners from any of these incredibly scenic vantage points: Along Stacy Boulevard and at the Cut Bridge, Stage Fort Park, Niles Beach, the Dogbar Breakwater at Eastern Point Light, the Bearskin Neck jetty, and Halibut Point.
6. Live Like a Local By Staying in a Vacation Home
Where you stay should be one of the best parts of your vacation! Atlantic Vacation Homes offers a special way to experience the North Shore. The fantastic (and cost effective) benefits of vacation rentals include extra space, a level of privacy that you won’t get in a hotel, and the amenities of a real home, like full kitchens and laundry equipment. With many properties now offering shorter 3-night stays, you can truly “live like a local” on your summer vacation or long weekend. Browse our shorter-stay vacation rentals on the Atlantic Vacation Homes website.
Bonus: Need more summer vacation activity ideas? Check out our list of 25 FREE Things to Do On and Around Cape Ann This Summer.
