Domestic Travel

Most Instagrammable Towns North of Boston

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My husband and I recently escaped to some charming towns north of Boston on a quick weekend getaway.

This was our first trip outside of Connecticut (our home) and New York (where my husband’s shop is) since January.

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.

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Picture-perfect towns in Massachusetts

Picture-Perfect 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.

Rockport Instagram Spots

1. Motif #1

Iconic Motif #1 is the thing to see while in Rockport.

Motif #1 along Bradley Wharf

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.

FUN FACT: Motif #1 is considered the most painted building in the United States. The shack is a favorite amongst artists because of the composition and lighting of its location.

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!

PHOTO TIP: One of the things I love most about this location is how photogenic it is from every angle! Therefore, I highly recommend you try capturing it from various spots.

My personal favorite shot (the one framed by the flowers below) was actually discovered completely by accident! If you’d like to create this shot yourself, head to the Judi Rotenberg Studio located at 9 Dock Square.

During the warmer months, there are beautiful flowers along the right-hand side of the studio. You can use these blooms to create a floral frame around Motif #1 in the distance.

For this shot, I recommend using a telephoto lens if possible. Although we didn’t use one ourselves, if we had, Motif #1 would’ve appeared more prominent. Instead, we used our 50 mm lens to create it. (It’s the first shot you see below.) 

Another great vantage point I suggest is directly across the water (as seen in the second photo below). You can reach this spot by taking the alleyway next to the former Engine House 1 off of Mt. Pleasant Street.

I also recommend walking along the parking lot side to create leading lines (as shown in the third photo below).

Finally, for an extreme close up, walk all the way down the pier to Motif #1 and take your shot from the stone landing.

Motif #1 surrounded by flowers in Rockport
Motif #1 in Rockport
Motif #1 in Rockport, Massachusetts
Motif #1

How to Get Here:

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.

2. Back of the Judi Rotenberg Studio

The back of the Judi Rotenberg Studio offers a charming arched entryway and lovely views of some Rockport homes.

beautiful trellis in Rockport

PHOTO TIP: This is a private property, so do be mindful when taking your shots.

How to Get Here:

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.

3. Square Circle Gallery

Square Circle Gallery has been showcasing a variety of fine arts and crafts for 50 years.

Square Circle Gallery

PHOTO TIP: The side of the gallery offers a pretty yellow façade with some attractive planters during the spring/summer season.

To create the shot above, enter this area by way of the brick patio. We incorporated the white fence in the shot to create a natural framing and depth.

How to Get Here:

Square Circle Gallery is located at 11 Dock Square in Rockport. You’ll find it next to the Judi Rotenberg Studio.

4. The Pewter Shop

Arguably the most picturesque shop in all of Rockport, The Pewter Shop just oozes New England charm.

The Pewter Store in Rockport

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.

PHOTO TIP: To capture this pretty building in all its glory, you’ll need to take a shot from the center of the street. Be mindful of cars when you do!

How to Get Here:

The Pewter Shop is located at 16 Bearskin Neck in Rockport.

5. The Ice Cream Store

If you’re in need of a photo break pick-me-up, why not stop at New England’s cutest ice cream shop?

The Ice Cream Store in Rockport, Massachusetts

Sadly, the shop was closed when we took our shot, but I was happy to see it open up later in the day!

PHOTO TIP: This is a pretty straightforward shot, so there’s not too much to say. We used our 50 mm lens here.

How to Get Here:

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.

Ipswich Instagram Spots

1. The John Whipple House

The John Whipple House is one of the most photogenic attractions Ipswich has to offer.

John Whipple House in Ipswich

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.

John Whipple House

PHOTO TIP: The fun part about this location is that you can create some really cinematic shots. To create a compelling composition and frame, I recommend incorporating the entryway bushes, like we did above.

2. High Street Homes

In addition, the neighboring area of Ipswich also has some of the most charming residential homes I’ve ever seen.

yellow house in Ipswich, Massachusetts

I can honestly say I’ve never seen a purple house on any of my travels. It was definitely unique!

Purple house in Ipswich, Massachusetts

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.

3. Castle Hill on the Crane Estate

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!

How to Get Here:

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.

Newburyport Instagram Spot


Oldies Marketplace is an antique store that appears to have gained some “Insta fame.”

Oldies Marketplace in Newburyport

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.

PHOTO TIP: Sometimes the reality “behind the gram” isn’t always pretty. In this case, you’ll need to reckon with an enormous parking lot in front of Oldies to get “the shot.” I suggest going at early morning and/or using a mid-length lens (35 – 70 mm) to avoid capturing the parked cars.

How to Get Here:

Oldies Marketplace is located at 27 Water Street in Newburyport.

Additional Towns North of Boston to Consider

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!)
  • Essex
  • Salem

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!

Did you find this post useful? Pin it to your boards!

Picture-perfect towns in Massachusetts
Top Instagram spots north of Boston
Most Instagrammable towns north of Boston

41 thoughts on “Most Instagrammable Towns North of Boston

  1. All of your photos are so beautiful Elena! I need to make my way back up to Massachusetts. It’s such a quaint state and I love all the charming homes. 🙂

  2. Such great pictures! I love how cute and New Englandy all of these places look. Would love to go there sometime. Plus the castle you didn’t get to see this time reminds me of nowhere better than it does Pemberley, the way they show it in the Keira Knightley P&P version. 😍

    1. Wow, everything you listed here looks great! Especially your photos. Just looking at it gives an itch to travel again. I hope you could share some tips about photography too! I would love that.

  3. These towns are so lovely! Glad you are able to explore. Here in California, we have a lot of beautiful places but not necessarily historic places. When I go to New York to visit my sister, we go to New Jersey and Pennsylvania. I love seeing the architecture.

  4. I love the relaxed, beach town feel of these! And I can’t say I’ve ever seen a purple house before either haha, perfect chill summer vacay destinations!

  5. You have just officials renewed my desire to visit New England. We haven’t made it to Boston yet, but when we do I would love to include some of these awesome places as well. 🙂

  6. All these towns are so pretty and quaint. Your pictures are lovely and I would love to visit them someday.

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