1-3 day special cultural events and festivals in Gloucester, Mass.
WINTER
Small Business Saturday
December Middle Street Walk
December Holiday shop local
December Mens Night
December Ladies Night
December Friends and Family Night
December Employees night
December Lobster Trap Tree Lighting and buoy painting
December Menorah trap tree
December Kent Circle parade and tree lighting
February Winter Birding trip
February Valentine's chocolate tour
SPRING
Backshore 5 mile
Pride Stride for community non profits
Gloucester Public School arts festival
Tulip Festival on the Boulevard
concert series
Gloucester May Celebration at the UU Church Sing through the Seasons
restaurant specials gearing up for summer seasons
Memorial Day observances
Topside Grill spring Triple Crown parties (Kentucky Derby, Preakness, Belmont Stakes)
Cape Ann Artisans spring/summer tour
SUMMER
Gloucester Summer Nights
Free Performances daily
Mondays farmers market Magnolia
Tuesdays
Wednesdays HarborWalk Summer Cinema Cape Ann Community Cinema and 104.9
Thursdays Farmers Market at Stage Fort Park and Harbor Loop summer concert series
Fridays Meetinghouse Green concert series United Universalist Church
Saturdays Main Street Block Parties
Sundays Stage Fort Park concerts at the bandstand
JUNE
Cape Ann Museum's weekly downtown summer guided walking tours 10 AM Friday and Saturday mornings
Cape Ann Farmers Market Mondays (Magnolia) / Thursdays (Stage Fort Park)
Small Business Week
Topside Grill spring Triple Crown parties (Kentucky Derby, Preakness, Belmont Stakes)
Cape Ann Artisans spring/summer tour
HarborWalk Summer Cinema free outdoor movie series
Bridge Strawberry Festival
July/Aug
July 4th (parade, fireworks, concert)
Downtown Main Street Block Parties July, August, September
Abbadia Mare Festival at Hammond Castle
Gloucester Waterfront Festival
Harbor Loop concerts
Stage Fort Park summer weekly concert series Antonio Gentile Bandstand Sundays/rain date Wed
UU summer concerts on Meetinghouse Green
Annual summer production Annisquam Village Players community theater since 1917
Celebrate the Clean Harbor Swim - history naturalist Sarah Fraser Robbins
Dinner en blanc at Maritime Gloucester
Gloucester Schooner Festival Labor Day weekend
FALL
Gloucester Schooner Festival Labor Day weekend
Maritime Heritage Day Maritime Gloucester museum
Labor Day events
Cyclocross Gran Prix of Gloucester at Stage Fort Park
Essex Heritage 2 weekends special free events Trails and Sails
Captain's Courageous Day
Gloucester YMCA Cape Ann 25K
Haunted Halloween at Hammond Castle
Main Street Trick or Treating
just in October!
Founded in 2016- Cape Ann Plein Air Note that Paint Essex annual Plein Air (founded in 2012) moved from a summer slot to the fall to coincide with Cape Ann Plein Air in 2016
Founded in 2016- Look for Magnolia Sip and Stroll nights – “Enjoy complimentary food, beverages and live music while visiting the wonderful shops on historic Lexington Avenue in Magnolia, MA”
Founded in 2015- Brace Cove 2nd Annual Art Market (one day only!) 1pm till dark.
Founded in – Oktoberfest at Cape Ann Brewing Company
Founded in 2010 /in Gloucester 2014 – Annual American Craft Week held in October Gloucester recognized as one of America’s top 10 towns for craft lovers | 2017 Annual American Craft Week October 6-15
Founded in 2015 – Pumpkin Carving at Cape Ann Art Haven
Founded in 2012- Fall Fest at Mile Marker 1 by Bridge Cape Ann
Founded in 2009- the Annual DoctoberFest Documentary Film Festival curated by Cape Ann Cinema & Stage (estab.2008)
Founded in 2006- Cape Ann Farmers Market outdoor market Thursdays into October, also features artisans and makers.
Founded in 1984- Annisquam Arts & Crafts show Oct 8 & Oct 9, 10-5
Founded in 1984- Annual Art Auction, Gloucester Lyceum & Sawyer Free Public Library
Founded in 1983- Cape Ann Artisans Studio Fall Tour (the oldest continuous in the country) featured as part of Artweek Boston 2016
Founded in 1979- Gloucester Stage is world class professional American theater in our country’s oldest seaport. Look for fall Premiers
Major year round attractions downtown include Gloucester's Fisherman at the Wheel memorial, Gloucester Beaches (3 downtown), restaurants, Main Street, Stage Fort Park and the Boulevard, Gloucester HarborWalk, Cape Ann Museum, Maritime Gloucester, Gloucester Stage, Gloucester Unitarian Universalist Church, Rocky Neck, Sawyer Free, Cape Ann Cinema film festivals.
Spring/Summer seasonal re-openings are celebratory- Look for whale watch and charter fishing, Hammond Castle, North Shore Arts Association, Sargent House Museum, Beauport Sleeper McCann, Schooner Adventure, and Schooner Lannon. Cape Ann Museum adds additional off-site and outdoors programming with fabulous guided walking tours and White Ellery installations.