During Summer 2025, I visited Rockport and Gloucester, Massachusetts for the first time. Don’t ask me why it took this long — I'm wondering that myself. It’s a short 2 hours drive from Mystic, Connecticut so it was a perfect day trip destination. I fell in love with the town so much that I knew I'd be back soon. I decided it would be worth the trip to see the holiday festivities during December.

I stopped at Woodman’s of Essex first for lunch. The entire menu was gluten free (with exception of like two items). It was worth the stop — the fried shrimp was delicious. The staff were friendly! I will be back here whenever I’m in the area.

Rockport is one of the most beautiful towns I’ve seen during Christmas time. There were trees in boats everywhere! I loved it. The town had a tree in downtown, the Motif 1 had a wreath and there were even trees out on the floating dock.

When I wasn’t photographing, I strolled around the town and popped in some of the shops. I was worried that with it being winter, that many shops would be closed. I was pleasantly surprised that it was more of 50-50. All of my specific favorites that I shopped in from last summer were still opened. There were plenty to do so I didn’t find myself disappointed with the visit to Rockport.

Rockport at Christmas time honestly was stunning and I would recommend a visit. I’m even thinking to come back next season — maybe a new tradition?!

Gloucester is nearby Rockport so I had to stop by to see the lobster trap tree that inspired the one in Stonington, CT. It was so similar with a few differences — Gloucester had three entrances/exits while Stonington only had one. The buoys on Gloucester’s tree all were created by children. Stonington’s buoys are mostly from local artists in Connecticut and Rhode Island. Regardless, the tree was beautiful and I enjoyed seeing it in person. I went just before sunset and went back after sunset to see it both ways.

Another reason for my visit to Gloucester was to see the lobster trap menorah. I’ve known about it for years and have been wanting to see it! So worth the visit — it was amazing sight! The menorah is located next block to the Main Street with shops in Gloucester. I popped in some of the shops, the antiques shops were particularly fun to check out.

It was a fun day in Rockport & Gloucester, MA. I can’t wait for many more visits back to the North Shore of Boston.