Cape Ann Day Trip

One of the great things about living in Boston is all of the amazing cities & towns that are within a 3 hour drive. Even better, you can get to either shore in about an hour (traffic depending). Lately we’ve been having spectacular weather- sunny, warm, breezy…perfect summer days! One of my favorite things to do on an open Saturday is explore! An area I’ve explored a lot is the North Shore. Whether you’re wanting a beach day, a boat day, a foodie day, or a shopping day, I’ve got your options covered! Here are a few of my favorite things to do in the North Shore, particularly Cape Ann.


Happy exploring!


Essex is a cute pit stop when passing through on your way north. Set along the Essex River, it’s your typical New England small town- shopping, restaurants, museums, and more!


If antiquing is your thing, you’re in luck! Considered America’s “Antiquing Capital”,  there are over 30 stores within 1 mile. I’ve been to about 10 different stores there- from low to high, from junk to treasure- it’s worth sifting through. You never know what you might find!

PicMonkey Collage- essex

Like seafood? Some top restaurants include JT Farnhams & Woodmans (in constant “Best of the best” battle) -be sure to try the fried clams!


Pronounced “glo-stah”,  this traditional harbor town is full of character, charm & breathtaking views. As you probably imaged, there’s an abundance of fresh seafood, wide sandy beaches & adorable ice cream shops all around.

There are two outstanding beaches: Wingaersheek beach or Good Harbor Beach (<- personal fave). I mean, look at these views:

Gloucester-GoodHarborBeach View from Wingaersheek Beach across the Annisquam River to the Annisquam Lighthouse, Gloucester, MA-L

If the beach isn’t your thing, why not check out the Whale Watching tours or the Fishermen’s Memorial statue. (Remember the Clooney/Wahlberg movie, The Perfect Storm? Filmed here & about these fisherman!)


When visiting Gloucester, one thing’s for sure: you won’t leave hungry! There are a plethora of delicious restaurants, but a few of my personal favorites are Duckworth’s for a special occasion, Seaport Grille for fresh lobster rolls & harbor views, Cape Ann Brewery for burgers + beers, and Short and Main for wood-fire pizza (fun fact: last time I ate there, I saw Frances McDormand & Ethan Cohen dining!)

PicMonkey Collage-glosta


Located about 15 minutes north of Gloucester, this darling beach town is a true gem. Remember the movie “The Proposal” ? Yup, filmed here! (the movie was set in Alaska, but the set was in Rockport).

PicMonkey Collage rockport

It’s full of lush flowers, fresh lobstahs, adorable shops & restaurants, and a k-i-l-l-e-r peninsula ocean view!

When you’re strolling around downtown, be sure pop in Bean & Leaf Cafe (<- try the Greek turkey wrap!), The Ice Cream Store & Roy Moore Lobster Co.

There’s a lot of shopping, so bypass thee tourist traps & spend your time in my favorite local stores: Lula’s Pantry and Milk & Honey , both of which have a great selection of home decor items & specialty kitchen/food products.

There you have it, my roundup of a perfect day trip to Cape Ann. Now go shop, eat & play!


One thought on “Cape Ann Day Trip

  1. Pingback: 5 New England Day Trips From Boston You Need to Take - Brunch on Sunday

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