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How To Spend 48 Hours in Rockport MA

How To Have An Epic 48 Hours In Rockport, MA

Ok, so you’ve decided you need a weekend away to decompress and reset. You’ve chosen Rockport, Massachusetts, wise decision. You’re off to a great start.

Welcome To Rockport MA

48 hours isn’t a lot of time to get the feel for a city or town, especially one with such rich and wide-ranging culture as Rockport, MA. But, if you’re on the hunt for things to in Rockport and you only have 48 hours, you’ll want to start close to the town center because parking can be a challenge.

The Addison Choate, at 49 Broadway, is the perfect location to walk downtown to the shops, restaurants, bars and galleries downtown.


FRIDAY AT 3PM: Check Into The Addison Choate

Let’s be honest, if you’re going to have a weekend getaway, it’s best to get a head start on the weekend crowd. No sense starting your weekend off on the wrong foot by sitting in Friday night commuter traffic one Route 128 wishing ill will upon your fellow beleaguered travelers.

Addison Choate Rockport MA Hotel

While the drive to Cape Ann and Rockport are not as painful as the atrocities you will be forced to endure on a trek to Cape Cod, it’s still worth getting a jump start.

The Addison Choate will let you check in as early as you want, so long as the room is ready.


FRIDAY AT 3:10PM: Check Out Your Room

Check out your new weekend digs. Good call on your choice of lodging, you’re going to love it.

Rockport MA inns and Bed and Breakfast


FRIDAY AT 3:30PM: Head To Bearskin Neck Shops

The shops of Bearskin Neck are about a 5-minute walk from Addison Choate. Take a stroll down Broadway and into Dock Square and be transported back to a simpler time.

Rockport MA Shops and Artists

Rockport is truly a Massachusetts’ treasure with an incredible variety of art galleries, ice cream parlors, craftsmen, and other independent shops. You could easily spend an entire afternoon wandering through them.

You can take a peek at a few of our favorites here: 12 Can’t Miss Rockport Shops!


FRIDAY 6:00PM: It’s 5:00 Somewhere

So, Rockport has a long and storied history surrounding prohibition that goes back to Hannah Jumper who lead a group of 200 hatchet wielding women through the town destroying every keg, cask and jug in town. That was in 1856 and the town remained dry until 2005. But those days are history and some exciting new establishments are cropping up on the dining scene.

Feather and Wedge Rockport MA

Feather and Wedge is a hip local restaurant whose name pays homage Rockport’s storied granite history.

Set the stage for the evening with a well-crafted cocktail and a half dozen (actually better make that a dozen) oysters. It’s your weekend, you’ve earned it. You can follow up your cocktail with a delicious dish from the talented and creative culinary team.

The dishes run the gambit from Vegetable Curry to Pappardelle Bolognese and everything in between. The menu changes regularly so there is always a imaginative new dish to try. We know that you want a lobster roll, there will be plenty of time for all of that later.

Not your cup of tea? No worries, here are 9 Restaurants near Rockport that we recommend. 



If you’ve never had the pleasure of seeing a show at this venue, it’s well worth it. The venue is features impressive construction, extraordinary acoustics and with just 330 seats you get the pleasure of an intimate experience with any artist performing.

Rockport MA Shalin Liu 48 Hours in Rockport

The venue’s draw is fantastic as well with world class artists like Branford Marsalis, John Scofield, Arlo Guthrie, David Benoit, and others gracing the stage. Oh yeah, and the backdrop of the stage is a floor to ceiling glass wall that features a stunning view of Sandy Bay. You can view the latest Shalin Liu Event Calendar here. 



Rise and shine. Stumble down to kitchen for a complimentary breakfast including fresh baked scones, croissant, bagels, fruit, granola, smoked meats, cheese, and good strong coffee. You can dine al fresco on the porch and enjoy the peaceful Rockport morning.




Time to cure that compounding vitamin D deficiency that has built up over the last few weeks at the office. Plus, hangovers cannot withstand the combined forces of sun and sea, it’s ummm science.

Cape Ann has a fantastic selection of beaches to choose from, no matter your beachgoing style. A few great ones to consider include: Long Beach in Rockport, Good Harbor in Gloucester, Singing Beach in Manchester, and Crane’s Beach in Ipswich.

All of these beaches are gorgeous in their own right. Let’s check out Singing Beach Today.


SATURDAY 10:00 AM: Bookstore Browsing

If you’re heading to Manchester By The Sea, you’ll want to pop into Manchester By The Book to get some appropriate beach reading. Meander through endless stacks of used books and find that perfect Updike or Travis McGee to toss into the beach bag.

Manchester By The Book Bookstore


SATURDAY 10:30AM: Drinking Carrot Juice & Soaking Up Rays

Off to the beach. The parking at Singing Beach is basically resident only, unless you have the coveted beach sticker that Manchester residents plaster on their cars like badges of honor, you’re out of luck.

So, you may have to park down by Harrigan’s Liquor or Masconomo park and walk up. It’s about a 7-10 minute walk, but it’s well worth it to enjoy this beautiful beach.

Manchester By The Sea Singing Beach

Beachgoers tend to be late risers, so hitting the beach at this time should give you plenty of time to claim the prime real estate, spread your legs and break out the football or frisbee.

This beautiful beach features a half mile stretch of sandy shoreline and sand that squeaks beneath (due to the grains unique make-up of quartz, zircon and feldspar) your feet as you walk, hence the name.

Being in Manchester can transport you back in time to the Victorian era. Many of the area elite built lavish homes in the late 19th century, before air conditioning, giving Manchester a Newportian vibe.


SATURDAY 2:00PM: Find Some Food and Shelter

Feeling good? You could grab a quick bite in town, but we say take the 15 minute drive out to Woodman’s in Essex, MA and get your lobster roll and fried clam fix.

Woodman’s is a classic New England clam shack and a Massachusetts institution. In fact, they even claim to have invented the fried clam!  

48 Hours In Rockport MA

Next door to Woodman’s there is also a brand-new brewery, Great Marsh Brewing. You can swing over, sample a couple of beers and maybe even grab a growler for the road. Check out the Great Marsh Website


SATURDAY 3:30 PM: Kayak Time!

Head down to Tuna Wharf and visit the team over at North Shore Kayak. That will set you up with a reasonably priced kayak or stand up paddle board and you can tour the inner harbor, head right out to the ocean, front beach or paddle out to Thatcher Island.

Rockport MA Kayak Tours Thatcher Island

It can help give you some great perspective of the landscape and there’s no place better on a beautiful day.


SATURDAY 7:00PM: Dinner on the Water

We’d recommend finding a deck with a view. One of our favorites in the area is at the Market on the Annisquam. The restaurant is owned and operated by The owners, Nico and Amelia Monday, got their start in Alice Water’s critically acclaimed, Chez Panisse.

The Market Annisquam

The farm to table cuisine is lovingly prepared and the menu changes daily. You can sit out on the deck, enjoy a Maine Brewing Company beer or nice glass of wine and overlook the Annisquam.


SATURDAY EVENING: Let There Be Songs To Fill The Air

Still Ready For Action? Of course you are. You only have 48 hours in Rockport, MA so you’ve gotta suck the marrow out of it!

Well, for nightlife we would recommend cruising right on into Gloucester. There are a number of great hot spots for nightlife, including the Rhumb Line, Drift and the newly redesigned Minglewood Harboside. 

48 Hours In Rockport MA - Minglewood Harborside

At Minglewood you can catch some live music at a comfortable and spacious restaurant/bar setting that is right on the water. You can check out their live music calendar here


SUNDAY 11:00AM: Quarry Time

Before you leave Rockport, we recommend that you swing up to Halibut Point. You can get a feel for Rockport’s rich quarrying history and some beautiful coastal views. It’s a 5-minute drive, up the aptly named Granite Street, and is well worth your time.

48 Hours In Rockport MA - Halibut Point

Sunday 3:00PM: Hit The Road Jack 

Well, that about wraps up our Epic 48 Hours in Rockport, MA. We hope that you found our guide helpful! Although we created this guide of fun activities, we have really just scratched the surface of what is available on Cape Ann. The area is so rich in so many ways that 48 hours really cannot do it justice. We hope to see you at our Rockport, MA hotel soon!


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