Exploring Massachusetts’ North Shore

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Plum Island, MA

On our recent trip to New England, Tyler and I spent two days in Vermont, two days on Plum Island on Massachusetts’ North Shore, and two very full days exploring Boston. Our best planned itinerary yet? Quite possibly.

I will always treasure our time on the North Shore. Plum Island, Massachusetts (not to be confused with Plum Island, New York– who dropped the ball on that one??) is a narrow strip of land that juts off the coast near Newburyport and runs parallel to Massachusetts for eleven miles. Neither of us had spent much time on the Atlantic (apart from a few summers visiting my grandparents in Ft. Lauderdale), so we were very excited.

Plum Island, MAPlum Island, MA

Tyler and I took it upon ourselves to obnoxiously embrace all things New England on this leg of the trip. So, yes, we did go lighthouse hunting and lobster-dining. Tyler even resurrected his old Sperry’s from the closet grave. 

We found ourselves swept away by the peaceful, moody beauty of this area, and Plum Island proved to be the ideal base for exploring. We’ve rounded up our favorite spots that we discovered on the North Shore for this post.

Plum Island, MAThe Cottage, Plum Island

Stay at Blue – Inn by the Sea

There’s no getting around it. The HIGHLIGHT of our time on the North Shore was our stay at the Blue – Inn by the Sea. This dreamy boutique hotel sits right on the water and is the most romantic spot for a coastal getaway. The property is tucked away in a pretty little neighborhood on the edge of town and provides the perfect starting point for long, leisurely walks on the beach. It’s also adjacent to the Sandy Point State Reservation.

Plum Island, MA

Nearly everything at this stunning hotel is bright white and accented with its signature color. The Blue is just one of those places that instantly makes you relaxed and at peace. It took us about seven seconds to feel at home in our spacious room and about one second to fall asleep to the sound of the crashing waves outside our window each night.

The Blue is actually part of the Lark Hotels group, and they have several gorgeous properties across the U.S. that are definitely worth checking out.

The Blue goes above and beyond when it comes to amenities. Wondering what do or what to eat in the area? Here’s an iPad, preprogrammed with recommendations and a guide to the area. Need to run over to The Cottage Island Market? (You need to, it’s so cute). Hop on a bright blue beach cruiser. Are those Atlantic waves a little too cold for your Californian feet? Take a dip in the beach-side hot tub and enjoy the view. Hungry when you wake up? Check outside your door for a fresh breakfast, delivered each morning by the staff in a basket. 

Blue Inn, MABlue Inn, MABlue Inn, MABlue Inn, MABreakfast, Plum Island

There is definitely a ton to explore on the North Shore, and we spent both days driving all over the area. We made certain, however, to rush back to the Blue by 4 or 5pm each night for absolute favorite part of the trip: sunsets on the beach. Ty ordered takeout, and we camped out on the beach with a bottle of wine in adirondack chairs for hours.

Blue Inn, Plum Island, MA

Seeing the “sun set” the opposite way of what we are used to on the Pacific blew our minds. Instead of waiting for the sun to drop below the horizon in front of us, we watched the sky turn from blue to orange to pink to purple and then a deep navy, sprinkled with stars.  Romantic, right? Wrong. Nothing like Tyler busting out an AR stargazing app to ruin the mood. Blessed.

Blue Inn, Plum Island, MA

Plum Island, MA

Tyler had his heart set on watching the sun rise, and he actually managed to wake me up, too. All he had to do was wake me up, wrap me in a towel, plop me in the hot tub, and hand me a cup of coffee. I’m a simple girl, what more is there to say?

Sunrise, Plum Island

Enjoy an unforgettable seafood lunch at Woodman’s of Essex

Friends of ours who lived in a Boston for a few years urged us to make the trip out to Essex for Woodman’s renowned seafood, so Tyler made sure to factor this stop into our itinerary for this trip (and mentioned it every day leading up to it, too).

We ordered our popcorn shrimp and lobster rolls at the counter and patiently waited with the rest of the 11:30am crowd (I think the nursing home shuttle had stopped on their way to bingo?). Tyler, with his ever-dramatic reactions to food, was a sight to behold as he power-walked through the booths of the restaurant with a tray of our food in his hands. He nearly knocked over half of the senior squad in his flurry.

Woodman’s is a must-stop in the area. It’s even worth the trip up from Boston for an afternoon. We practically swallowed our meals whole and loved every second of it.

Blue Inn, Plum Island, MA

Explore Halibut Point State Park

Determined to work off our lunch (ok, earn our ice cream later that afternoon, see below), we drove towards the coast to check out Halibut Point State Park in Rockport. It takes about twenty minutes to walk through the park to the ocean for stunning views of the Atlantic. As previously discussed, it was ridiculously hot that week. I had to cut our time exploring short before my already tight jeans melted to my skin permanently. Had it been a little cooler or had I the forethought to actually utilize the weather app on my phone for this trip, we could have spent hours exploring this area.

Halibut Point, MA

Treat yourself in Rockport

We already know I have blood sugar issues (learn more about how Tyler deals with it here). Perhaps now is a good time to reveal that I also struggle with regulating my body temperature. I know, just fraught with peril over here. But when I get hot– which is a lot– I get grumpy. After the sweat session at Halibut Point, Tyler knew the only answer was to get me some ice cream FAST. Ladies, get yourself a man who knows the art of the well-timed ice cream cone.

Luckily, Rockport, MA is just teeming with treats. We got shakes at The Ice Cream Store (please go here) and iced coffee at Brothers Brew Coffee Shop (definitely order the Dark Sin iced coffee). We loved walking through the adorable streets of Rockport, too.

Ice Cream Store, Rockport

Drive the coast from Rockport to Manchester-by-the-Sea through Magnolia

We recommend spending an afternoon exploring the coastline between Rockport and Manchester-by-the-Sea. Take the route that travels through Magnolia, and have fun staring at all of the larger-than-life mansions towering over the water. We didn’t pack our suits that day, but our friends also recommended that we swim at Singing Beach nearby.

Plum Island, MA

As much as we love taking on a major city hour by hour, there was something truly refreshing about relaxing at the Blue Inn and exploring the North Shore. Slowly but surely, we are learning how to plan on a long trip and be intentional about rotating “slower” stays into our itinerary. We noticed that we came back from this week long trip not feeling like we need five days to catch up on sleep, as we usually are. Funny what a little relaxation can do for you, right?

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Massachusetts' North Shore



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