We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Review Highlights
Small city downtown area.

Main Street has a mix of businesses that cater to locals and tourists. Restaurants, gift shops... read more

Reviewed 2 weeks ago
Very charming street with plenty of shops and restaurants

Need a cup of coffee or a snack, there are multiple choices; Looking for something to wear... read more

Reviewed 4 weeks ago
Alexandria, Virginia
Read all 142 reviews
All photos (24)
Full view
Certificate of Excellence
Traveller Overview
  • Excellent40%
  • Very good43%
  • Average16%
  • Poor1%
  • Terrible0%
Travellers talk about
“antique shops”(5 reviews)
“brass monkey”(4 reviews)
“mystery train”(3 reviews)
Local Weather
Powered by Weather Underground
Main Street, Gloucester, MA
Top Selling Tours & Activities in and around Gloucester
from US$38.00
More Info
from US$29.00
More Info
from US$35.00
More Info
Reviews (142)
Filter reviews
139 results
Traveller rating
Traveller type
Time of year
More languages
Show reviews that mention
All reviewsantique shopsbrass monkeymystery traincharming streetbook storecozy restaurantsnice place for a walkwe enjoyed walkingolive oil companysugar magnoliasdowntown gloucesterparking spacenew englandgloucester houseoff seasoncape annbusinesses
Updating list...
1 - 10 of 139 reviews
Reviewed 2 weeks ago

Main Street has a mix of businesses that cater to locals and tourists. Restaurants, gift shops, clothing stores, bars with entertainment and Five Cent parking meters.

1  Thank M_Freedley
Reviewed 4 weeks ago

Main street still has the turn of the century store fronts and many specialty stores the city is changing with the times as more new generation restaurants open up and the existing stores are catering to the new generation of shoppers and diners quite a...More

2  Thank bubbia1
Reviewed 4 weeks ago

Need a cup of coffee or a snack, there are multiple choices; Looking for something to wear, multiple choices; Looking for a restaurant, multiple choices; Looking for gifts or souvenirs, multiple choices; Would you like to go antinquing? There are multiple choices there too. And...More

Thank RabbiGary
Reviewed May 7, 2018

Lots of interesting shops and places to eat. Used clothing books, great new shoe shop, and many ars and crafts available here. Don't miss it!

Thank scelex
Reviewed April 29, 2018 via mobile

This is a nice coastal town to stroll through. They have some nice shops and art galleries rather than just the tourist trinket shops you find in some towns. An enjoyable town without the crowds (off season). Don't know what it is like in the...More

Thank Jim B
Reviewed April 21, 2018

Wow, this is the way I remember seaside towns being. Gloucester hasn't been all upscaled and dolled up and make pricey and clean. And that's what I LOVE about it. There are so many stores in downtown Gloucester that wouldn't stand a chance in, say,...More

Thank Dave S
Reviewed April 16, 2018

This street is lined with restaurants, tourist shops, galleries, bookstores. As it winds through the town you see new things and some interesting buildings. We found it charming in it's simplicity.

Thank Robert S
Reviewed April 2, 2018

The west end of Main Street has something for everyone...restaurants, high end or more affordable, lovely gift shops and jewellers, an olive oil company, even a funky second hand store with vintage clothing for when you want to go "bananas".

1  Thank Lynne K
Reviewed January 21, 2018 via mobile

Visited Main St yesterday! It was cold and windy, but we had a great time! The best thing about THIS Main St is that the majority of the stores are actually open even in winter, unlike many of the other nearby towns. Lots of charming...More

5  Thank LoriAllen
Reviewed November 4, 2017

Lots of shops especially gift and antique shops. Go to the Brass Monkey Gift Shop...one of the best in New England. Have dinner or lunch at the Gloucester House. Awesome food.

Thank jerdc
View more reviews
Questions & Answers
Ask a question
June 26, 2017|
Response from Diana S | Reviewed this property |
Have not been in Rockport on July 4, but I can say it's important to read the signs. I parked near the harbor and got a $50 ticket. I should have walked around and read the signs that said "resident sticker" only. Good... More