Day Trip: Gloucester, MA

A few weekends ago I spent the weekend hanging out with a good friend, and we spent Saturday lollygagging around one of our favorite seaside towns – Gloucester (glaw-sstuh), Massachusetts. Do people still use phrases like lollygagging? Is it just me? Mom, what have you done to my vocabulary!?

I’ve really missed living on the North Shore of Boston, so it was a pleasure to run rampant on our old stomping grounds.

I love Gloucester. It’s the no frills fishing town you’d expect it to be (a la The Perfect Storm).

It was supposed to snow, but fortunately it was mostly just a “wintry mix”… don’t you hate that weather prediction? What in the world is a “wintry mix”?

For breakfast you need to hit up my favorite – Sugar Magnolias. If you’re craving sweet, get the Carrot Cake pancakes. It’s you want savory, get the Irish Bene. (Oh boy, I’m drooling just thinking about it.) And if the line’s too long, walk around the corner to The Two Sisters. Smaller place, but equally satisfying.


Make your way down Main Street and pop in three of my favorite stores:

Dogtown Books – where you might be able to find a vintage hardcover of your favorite childhood chapter book or the new best-seller that’s on your list of things to read.

My favorite store – no really, I don’t even know what the name of this store is because I just refer to it as “my favorite store”. … after a brief stint in Google, I’ve determined the store’s name is Main Street Arts & Antiques. Even though this store isn’t that large, I could sift through it for the whole afternoon.

On this particular weekend, my friend and I satisfied ourselves with the boxes and boxes of vintage postcards. Oh my stars, postcards were so much more clever/pretty back in the day! This store is full of treasures and I usually don’t walk out empty handed. On this particular day I came home with a handful of vintage postcards now hanging in my office.

Lastly, if you love vintage clothing and accessories you have to hit Bananas. You can’t miss it, as there is a giant yellow banana hanging outside the establishment. If you’re looking for suede fringe hippie pants, an I-am-16-going-on-17 Sound of Music dress or a Jackie O. pillbox hat, Bananas is your place. And don’t get my started on the jewelry cases. If you’re looking for vintage jewelry, this is your mecca.

Before we left, we made to stop by the Lone Gull coffeehouse for some joe and sandwiches. I had the BLT and it was quite tasty. (They make it with ranch dressing, strange, huh?). And the apricot pastry was a unique sweet to wrap up the meal.


If you have some more time:

Glazed Pottery Studio is the perfect way to spend a relaxing evening with girlfriends.

And driving over to Annisquam is a visual delight.

And if you’re there in August – make sure to be there for St. Peter Fiesta and the Greasy Pole if you want to see Gloucester at it’s finest!

You can’t make this stuff up. via

(And by finest, I mean the Gloucester men sloshing around in costumes trying to grab a flag at the end of a greased-up and lard-covered log that is suspended 30 feet over the Atlantic Ocean! It’s a must-see. Just trust me.)

And don’t forget to say hello to this guy and while taking a walk through Stage Fort Park.


Thanks for a wicked awesome Saturday, Gloucester. I miss you.


11 thoughts on “Day Trip: Gloucester, MA

  1. I miss Glostaaaaaaaa soooo much. I was just thinking of my first place (aka someone’s beach home that I rented) in Annisquam. Really, really miss it. Great photos- thanks for taking me back! 🙂

  2. AHHH! Im so excited right now! I am obsessed with your blog and I’m FROM Gloucester! Actually, Rockport, but I live in Gloucester! Next time your here tell me! I can point you to the real beauties on the “island” as we like to call it!

  3. I got ahead of my self and didnt even read the post! PS. Fiest Is the last weekend in June/beginning of July, My best friend one the saturday greasy pole this year!

  4. It’s pathetic really! Too many projects and too much traveling! We have yet to both go back up together and drive by our old place! Hopefully sometime soon!

  5. Ahh, thank you! I ❤ the Greasy Pole! I definitely want to get the guidance of a native! I think I love Rockport even more than I love Gloucester!

Comments are closed.