45th Annual Gloucester Waterfront Festival - SAT/ 2026

Event Sponsors

Date and Time

Saturday Aug 15, 2026
9:00 AM - 6:00 PM EDT

SATURDAY | AUGUST 15th | 9 AM-6 PM
7:30am-11am - Pancake Breakfast by the Rotary Club of Gloucester
9am-6pm - Festival Open: Arts, Crafts, Food Booths & Kid's Area

    ENTERTAINMENT:
    9:00am-11am - Music of Chris Taylor
    11am-1pm - Don Boudreau EP Rock - Elvis Tribute Artist
    12pm-3pm - Captain Jack Sparrow, Pirate roaming the Festival
    1pm-3pm - Mike McGeowan Band - Classic Rock, R&B
3pm-6pm - The Ride - Cover Band

*Roving throughout the day...
        - Children's Entertainment by Pirate Man Dan with his Bubble Ship
      - Helen's Willow Wind will be enchanting guests with her award winning flute music

SUNDAY| AUGUST 16th | 9 AM-5 PM
9am-5pm - Festival Open: Arts, Crafts, Food Booths & Kid's Area
9am-2pm - North Shore Old Car Club displays dozens of antique/classic autos

    ENTERTAINMENT:
    9:00am-11am - Music of Chris Taylor
    11am-2pm - Jonee Earthquake Band- Rock, Country, Ska
    12pm-3pm - Captain Jack Sparrow, Pirate roaming the Festival
  2pm-5pm - The Bordellos - Classic Country & Roots Rock

   *Roving throughout the day...
        - Children's Entertainment by Pirate Man Dan with his Bubble Ship
      - Helen's Willow Wind will be enchanting guests with her award winning flute music

Location

Stage Fort Park
Hough Ave
Gloucester, MA

Hough Ave Gloucester MA 01930

Fees/Admission

There is no entry fee for the Fair.
There is a parking fee at the beach parking lot.
Make online parking reservations here: https://gloucester.blinkay.app/login

Website

castleberryfairs.com

Contact Information

Michelle Pepin 978-283-1601
Send Email

Enter your email address below to receive a reminder message.

Please complete the Captcha

Event Sponsors

Description

The historic Stage Fort Park along Gloucester Harbor will blossom into color and flavor for the 45th Annual Gloucester Waterfront Festival on Saturday, August 15th and Sunday, August 16th, 2026.

This event features over 150 Booths of American made arts, crafts, foods and live music. Admission is free, handicap accessible, held rain or shine and friendly pets are welcome on leash at this seaside New England event. For more information visit: www.castleberryfairs.com
Note: There is a fee to Park at beach parking. https://gloucester.blinkay.app/login

The Gloucester Waterfront Festival is Sponsored by Greater Cape Ann Chamber of Commerce