Fun Day Trips North of Boston, MA

I grew up on the North Shore of Massachusetts, right between Boston and Cape Ann. So when we would take a day trip, it was usually during the summer (despite being life-long New Englanders, we were never big winter people) and usually somewhere along the coast. While I’ll do a more in-depth post on each of these destinations (though you can already read more about my love of Salem here, here, and here, and you can see more photos of Russell Orchards here), for now, I’ll still to the highlights of each destination. Here are some of my favorite, fun day trips North of Boston. Think of this as your travel guide to the North Shore of Massachusetts. 

Please note that most of these images were taken pre-Covid. 

Newburyport

When to go: Though it’s beautiful all year round and especially quaint at Christmastime, because it’s right on the ocean it can get rather brisk in the winter. The warmer months are preferable but to avoid crowds, try to hit this seaside gem during the week. If you want to see it in full swing, the first weekend of August is homecoming and they have street festivals and fireworks over the boardwalk. 

What to see: Downtown and the boardwalk are beautiful for sightseeing. 

Where to shop: The downtown is full of adorable little shops and boutiques. You can find home goods, clothing for the whole family, and fine jewelry. I never visit without a stop into the Oldies Antique Marketplace and Dyno Records. 

Where to eat: Sea Level has a beautiful view of the boardwalk on one side of the building and the downtown on the other, so you really can’t go wrong there. Michael’s Harborside and The Starboard Galley are two Newburyport mainstays that also have incredible views and incredible food. 

Marblehead

When to go: This is another seaside town so while it can be beautiful in the snow, make sure you add this to your summer bucket list. 

What to see: Take a walk downtown or along the coast. Also, the Old Town House, right in the center of Market Square, is often referred to as “Marblehead’s Cradle of Liberty” because many pre-revolutionary war meetings were held there. It’s not only a beautiful location, but it’s also full of history. 

Where to shop: While Marblehead may not have as many boutiques right downtown as some of the other destinations on this list, it still has some fascinating finds. My favorite is Haley’s Wine & Spirits, which has the most unique wine and beer selection in the area. There is also a small cafe in the same building that is so cute for cookies and other baked goods. 

Where to eat: Though I haven’t been in a few years, I am still dreaming of the flourless chocolate cake at 5 Corners Kitchen, a modern, trendy eatery that has a lovely brunch. 

Salem 

When to go: October may be the obvious choice but Salem has events happening all year round. And truthfully, it gets too busy during the Halloween season. I love Salem in September. The city is getting ready to embrace its title as Witch City, but tourists still haven’t arrived yet.

What to see: It completely depends on what you are interested in. This city has history, beautiful views, monuments, a world-class museum in the PEM, and lots of experiences dedicated to the Salem Witch Trials. There are also haunted houses and you can even check out some of the filming locations for the cult classic, Hocus Pocus. 

Where to shop: Again, it depends on the experience you are looking for. If you are coming to enjoy Salem as a pretty city to visit, Modern Millie’s is a fun shop for vintage wears and rockabilly looks, while the Trolley Depot is fantastic for souvenirs. I also love Pamplemousse for its unique items and gourmet finds. If you’re looking for the witchy stuff, you’re in luck. Stores range from the kitschy like The Magic Parlor to the somewhat intense with Hex Old World Witchery, to the modern-day Vogue-loving witch with Hauswitch – my favorite. 

Where to eat: Gulu Gulu Cafe or Flying Saucer Pizza Co. are my two favorite places to enjoy a meal in Salem. But I also enjoy Sea Level, Rockefella’s (we had our reception right upstairs!), and Front Street Coffee House has the best chai latte around. 

Crane Estate and Crane’s Beach

When to go: For the Crane Estate, any time of the year is beautiful. Though I usually love to wander the grounds in good weather, the mansion is gorgeous covered in snow. Obviously, summer is the best time for a visit to Crane’s Beach. 

What to see: If you’re only going to be in the area for a day, why not make an outing of it! If it’s a really hot one, spend your morning cooling down at the beach and then the afternoon touring Estate. Or you can flip it and spend your afternoon relaxing on the beach after your Estate tour!

Where to shop: The Estate has a small gift shop that has everything from books about the Crane family and home to jewelry to other small trinkets. The Beach also has a little shop equipped with towels, bathing suits, sweatshirts, water toys and flotation devices, anything you may have forgotten at home.

Where to eat: While the Estate does have a cafe, it is closed due to Covid-19 restrictions. The Beach has a little ice cream and refreshment stand that I believe will be open this summer. Otherwise, bring a picnic! Just make sure you clean up after yourselves to keep the grounds looking pristine for other visitors. 

Russell Orchards

When to go: Russell Orchards will reopen May 1 and usually stays open until the end of November. My favorite time to go is in September or October when the pumpkins have arrived as well as the apple cider doughnuts! But try to avoid weekends during that time because it gets rather busy. 

What to see: This is such an idyllic place with a large barn full of award-winning wines and delicious baked goods, as well as expansive grounds. It’s a beautiful place to take the whole family for an hour or so of sightseeing and animal introductions. 

Where to shop: As I said, the shop is packed with fun goodies – including an ice cream stand, fresh groceries, fine wines, 

Where to eat: They have the best apple cider doughnuts in New England … I kid you not. Sometimes they also serve up apple cider sundaes which is the best idea ever. 

Rockport 

When to go: Summer is when this tiny waterfront village shines, but they also have a beautiful tradition in December when all of the residents put on a nativity pageant that makes its way down the main street to a lifesize stable in front of the church. 

What to see: Bearskin Neck is the place to be! Beaches, lots of cute boutiques, and perfect for a summer stroll. 

Where to shop: Bearskin Neck Country Store, Floating Lotus, and The Blue Lantern are my favorites, but you really cannot go wrong. There are touristy shops where you can find Rockport tees and sweatshirts, but they also have some gorgeous clothing boutiques and fine jewelry stores. 

Where to eat: Roy Moore Lobster Shack is the best place to get your lobster fix, while Helmut’s Strudel provides delicious coffee and pastries if you’re in the area for breakfast. My Place by the Sea has a beautiful view of the ocean and is an excellent choice for a night out on the town. Instead of getting dessert wherever you end up, head to The Fudgery for the best fudge in the area. 

Kennebunkport

Note: I know I said I would stick to Massachusetts destinations but this one is not too far over the border into Maine. 

When to go: I’ve only ever been in the spring but I imagine this adorable area is a seasonal destination, bustling with business in the summer. 

What to see: The beaches are beautiful and well maintained. Barbara Bush would often be seen walking the family dog along the beach in the summer. Dock Square is where you’ll find great shops and restaurants as well as a bit of sightseeing.

Where to shop: Fine Print Booksellers is the most adorable small book shop with a ton of popular picks as well as unusual finds. The Candyman is like an old-fashioned candy store with delicious treats and fudge. They also have some fantastic clothing stores and I’ve heard their antique stores are second-to-none.

Where to eat: Alisson’s is actually where the Bush family (George H.W. and Barbara), would dine when they were staying at their summer home in Kennebunkport. Mornings in Paris has some great lattes, baked goods, and sandwiches – the perfect stop coming into town if you’re arriving around breakfast time. You could always grab your morning meal there before you head to the beach, then grab a lobster roll at Alisson’s before hitting the shops!

What are some of your favorite day trips in Massachusetts or beyond? We’re always looking for somewhere new to explore so please DM me your travel tips!