Skip to content
  • Weddings
  • Group Tours
  • Plan Your Visit
    • Travel Info
    • Transportation
    • FAQs
    • Summer
    • Travel Info
    • Transportation
    • FAQs
    • Summer
  • Things to do
    • Beaches and Outdoors
    • On the Water
    • Arts & Culture
    • Museums & Attractions
    • Historic Sites & Landmarks
    • Festivals
    • View all Things to Do
    • Beaches and Outdoors
    • On the Water
    • Arts & Culture
    • Museums & Attractions
    • Historic Sites & Landmarks
    • Festivals
    • View all Things to Do
  • Dine
    • Restaurants & Bars
    • Sweets & Treats
    • View All Dining
    • Restaurants & Bars
    • Sweets & Treats
    • View All Dining
  • Shop
    • Clothing & Accessories
    • Markets & Bakeries
    • Gifts & Souvenirs
    • View All Shops
    • Clothing & Accessories
    • Markets & Bakeries
    • Gifts & Souvenirs
    • View All Shops
  • Stay
  • Events
    • Calendar
    • Festivals
    • Culture Splash
    • Calendar
    • Festivals
    • Culture Splash
  • Neighborhoods
    • Downtown
    • East Gloucester
    • Dogtown, Annisquam, Lanesville
    • Magnolia
    • West Gloucester
    • Downtown
    • East Gloucester
    • Dogtown, Annisquam, Lanesville
    • Magnolia
    • West Gloucester
  • Blog
Get the Guide
11 events found.

Festivals

  1. Events
  2. Festivals

Events

Events Search and Views Navigation

Event Views Navigation

  • List
  • Month
  • Day
  • Photo
Today
  • May 2026

  • Sat 16

    Motif No. 1 Day

    May 16
    Downtown Rockport Rockport, MA, United States

    Join us for Motif No. 1 Day as we celebrate Rockport’s unique identity as both a historic fishing village and a vibrant artist destination. Centered around the iconic red fishing shack—long a favorite subject for painters and photographers—this beloved annual event brings together the very spirit of Rockport: coastal beauty, creative energy, and community pride. […]

  • October 2026

  • Sat 3
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 3 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Sun 4
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 4 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Mon 5
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 5 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Tue 6
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 6 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Wed 7
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 7 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Thu 8
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 8 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Fri 9
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 9 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Sat 10
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 10 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • Sun 11
    Cape Ann Plein Air

    Cape Ann Plein Air

    October 11 Cape Ann Plein Air
    Locations Vary

    Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!

  • November 2026

  • Sat 7

    From the Deep: A Downtown Gloucester Arts Party

    November 7 @ 11:00 am - 5:00 pm
    Harbortown Cultural District

    From the Deep: A Downtown Gloucester Arts Party Saturday, November 7, 2026 11:00 am to 5:00 pm across the Harbortown Cultural District Dive into a day of art and culture in the heart of downtown Gloucester. From the Deep returns this fall, inviting you to wander the walkable Harbortown Cultural District and discover live art […]

  • Today
  • Next Events
  • Google Calendar
  • iCalendar
  • Outlook 365
  • Outlook Live
  • Export .ics file
  • Export Outlook .ics file

Keep in touch

Stay up to date with events, festivals and news!
  • Dining
  • Shop
  • Stay
  • Events
  • Things to Do
  • Dining
  • Shop
  • Stay
  • Events
  • Things to Do
  • Weddings
  • Group Tours
  • Plan Your Visit
  • FAQs
  • About Discover Gloucester
  • Partners
  • Weddings
  • Group Tours
  • Plan Your Visit
  • FAQs
  • About Discover Gloucester
  • Partners

info@discovergloucester.com

Loading Comments...