My husband and I recently escaped to some charming towns north of Boston on a quick weekend getaway.
In fact, our last real trip was to Vermont in January – back when we had high hopes for 2020!
However, as we all know, sometimes life has other plans. We’ve all had to pivot – especially us travel bloggers – and acclimate to the times.
While it’ll take time for the travel industry to recover, I’m happy to start that process a bit closer to home.
Although we’ve explored much of New England, I was happy to visit three Massachusetts towns for the first time.
Each of these historic seaside gems is less than an hour from Boston and perfect for relaxing and/or enjoying water activities.
So whether you’re actively planning a road trip or looking for some East Coast inspiration, here are three Instagrammable towns north of Boston.
Charming Rockport is located in Essex County, Massachusetts, just under an hour’s drive from Boston. There’s also a 75-minute commuter rail train you can take from Boston.
Rockport is located on the tip of the Cape Ann peninsula along with the more well-known town of Gloucester to the south.
This picturesque seaside town is quaint and relatively quiet, making it the perfect escape from fast-paced city life. It offers cliffside beaches, tasty seafood restaurants, and plenty of unique shops.
Speaking of, if you’re interested in some shopping while you’re here, here’s a list of shops and boutiques in the area.
Unfortunately, save for some coffee shops and ice cream shops, many restaurants were closed while we were here (given the current world situation).
Fortunately, we were able to find more outdoor dining options in the neighboring town of Gloucester.
That said, there are plenty of photo opportunities to be had here!
Below are my favorite Rockport gems that you’ll want to snap for your Instagram.
Iconic Motif #1 is the thing to see while in Rockport.
Admittedly, when I first read about it in another blog post, I thought the writer was using a code name (or it was a typo).
As it turns out, neither was true.
Motif #1 may sound like a strange name for a fishing shack, but there’s actually a story behind it. Essentially, it was such a popular subject of paintings that it became a “motif,” or repetitive work of art.
The adorable red structure you see today is actually a replica of a former fishing shack.
Although the original fishing shack was destroyed after a blizzard in 1978, this replica was rebuilt to pay homage to the lost icon.
Motif #1 was featured in movies, a cigarette ad, and on a postage stamp.
Not too shabby for a relatively unknown town like Rockport!
Motif #1 is located along Bradley Wharf in Rockport. If you’re driving directly to this spot, there’s a parking lot (as mentioned above) at 1-T Wharf. You can view the Google Maps link here.
The back of the Judi Rotenberg Studio offers a charming arched entryway and lovely views of some Rockport homes.
You’ll notice a little alleyway along the right-hand corner of the Judi Rotenberg Studio (9 Dock Square) that offers a view of Motif #1. You’ll find this charming spot about 30 feet down the alleyway on your left-hand side.
Square Circle Gallery has been showcasing a variety of fine arts and crafts for 50 years.
Square Circle Gallery is located at 11 Dock Square in Rockport. You’ll find it next to the Judi Rotenberg Studio.
Arguably the most picturesque shop in all of Rockport, The Pewter Shop just oozes New England charm.
This special family-owned business has been standing tall since its opening in 1935. They sell a range of jewelry, home goods, metal prints, and unique gifts.
The way this quaint shop was sandwiched between two streets reminded me very much of the architecture in Paris.
If you’d like to browse the shop, weekday hours are from 9 AM to 5 PM Monday to Friday. Weekend hours are from 10 AM to 5 PM on Saturdays and from 11 AM to 5 PM on Sundays.
The Pewter Shop is located at 16 Bearskin Neck in Rockport.
If you’re in need of a photo break pick-me-up, why not stop at New England’s cutest ice cream shop?
Sadly, the shop was closed when we took our shot, but I was happy to see it open up later in the day!
The Ice Cream Store is located at 14 Bearskin Neck in Rockport.
We also visited the pretty town of Ipswich, my favorite spot on our weekend itinerary.
Ipswich is just under a half hour from Rockport and about 50 minutes north of Boston by car.
This historic town was founded back in 1634 and is commonly known as “America’s best-preserved Puritan town.”
You can read more about Ipswich’s interesting history here.
The John Whipple House is one of the most photogenic attractions Ipswich has to offer.
This historic colonial house/museum seriously reminded me of something straight out of an M. Night Shyamalan film.
It dates back to 1677 and is one of the best examples of “first period” American architecture.
If you’re looking to visit the museum, check here for hours and availability before your visit.
Obviously, I couldn’t miss a photo opportunity here.
In addition, the neighboring area of Ipswich also has some of the most charming residential homes I’ve ever seen.
I can honestly say I’ve never seen a purple house on any of my travels. It was definitely unique!
Both of these homes are located on High Street.
There are also a number of historic homes you can check out here as well.
Unfortunately, we didn’t hit these on this particular visit, as I didn’t discover them until after the trip.
I also wanted to photograph Castle Hill on the Crane Estate while in Ipswich, but we ran short on time.
Unfortunately, they only allow guests during predetermined times, so you’ll need to make a reservation.
However, if I visit on a future trip, I’ll be sure to update this post with my insight!
The John Whipple House is located at 53 South Main Street.
Castle Hill on the Crane Estate is located at 290 Argilla Rd.
Located 35 miles north of Boston (and just under a 50-minute drive) is the small maritime town of Newburyport.
It’s known for its boating community and award-winning dining and shopping. You can read more about this scenic town here.
Oldies Marketplace is an antique store that appears to have gained some “Insta fame.”
It was closed when we came by, but we were still able to photograph it. For more information on what they sell and open hours, head here.
Oldies Marketplace is located at 27 Water Street in Newburyport.
If you have time, I also suggest visiting the following towns north of Boston:
- Gloucester (We had dinner here, but didn’t take any photos. I wanted to visit the Hammond Castle Museum, but it was closed. However, it will be open in the third phase of the state’s reopening plan!)
If you’re looking to discover more of New England, I recommend checking out some of these quaint seaside towns. You’ll enjoy snapping pretty photos, relaxing by the water, and indulging in all the seafood!
Have you ever visited these or other towns north of Boston? I’d love to hear about your experience!