The calendar year is full in Westport with art and craft shows, blues festivals, free outdoor music and summer fireworks. Below is a taste of what the town offers:
Town Annual Calendar
Community Events | Ongoing | Town-wide
SPRING
Arbor Day Celebration | Apr | Town Hall
Art Show Fundraiser by Westport Women’s Club | Apr | Bedford Hall
Concerts by Westport Women’s Club | Ongoing | Bedford Hall
Dog Festival | May | Winslow Park
Farmer’s Market | Spring-Summer, Thursdays | 50 Imperial Ave
Fashionably Westport Shopping Day Events | May | Downtown
Fashionably Westport Runway Fashion Event | May | TBD
Fine Arts Festival, 48th Annual | May 29 & 30 | Downtown
Garden Club Plant Sale | May | Saugatuck Congregational Church
Great Westport Sandwich Contest | Mar | Online
Greens Farms Volunteer Fire Company Easter Egg Hunt | Spring | Long Lots Elem.
Minuteman 5K | Apr | Compo Beach
Near and Far Charity Gala | Mar | Mitchells, 670 Post Rd E
Soup Contest | Mar-Apr | Online
Spring Fashion Show | Mar | Westport Woman’s Club, 44 Imperial Ave
Taste of Westport | May| Longshore
Wakeman Town Farms Ongoing Events | Cooking & Farm Camps, Oktoberfest, Harvest Dinner Fundraiser | All Year | 134 Cross Hwy
SUMMER
Booked for the Evening | June | Westport Library
Great Duck Race | June | Parker Harding Plaza
Historical Society Hidden Garden Tour | June | Westport & Weston
Independence Day Fireworks Celebration | July | Compo Beach
Library Book Sales | July & Sept | Jesup Green
Makers Faire | June | Downtown or Staples H.S.
Remarkable Drive-In Theater | Summer | Imperial Parking Lot
Sidewalk Sale | June | Downtown
Unitarian Church Annual Tag Sale | Aug | 10 Lyons Plains Rd
Yankee Doodle Fair | June | Imperial Parking Lot
YMCA Point-to-Point Swim | July | Compo Beach
FALL
Christmas Tree Lighting | Nov/Dec | Town Hall
Clothing Tag Sale Fundraiser | Nov | Westport Woman’s Club, 44 Imperial Ave
CraftWestport | Nov | Staples High School
Farmer’s Market | Nov-Mar, Thursdays | Gilberties, 7 Sylvan Rd S
Fitness Week | Nov | Free Classes at YMCA & Townwide
Halloween Parade | Oct | Veterans Green
Halloween Window Painting | Oct | Main Street
Harvest Annual Fair & Shabby Chic Boutique | Nov | St. Luke Church, 49 Turkey Hill Rd N
Homes With Hope | Nov | The Regina A. Quick Center, Fairfield University
LobsterFest | Sept | Compo Beach
Make a Difference Day | Oct | Westport
Pink Aid Charity & Fashion Show | Oct | Mitchells, 670 Post Rd E
Restaurant Week | Sept-Oct | Westport
Saugatuck Story Fest | Sept | Library
Sip & Savor | Nov | Westport Woman’s Club, 44 Imperial Ave
Slice of Saugatuck | Sept | Saugatuck
Supper & Soul | Oct | Downtown
Westoberfest | Sept/Oct | Elm Street
Westport Kiwanis Club Triathlon | Sept | Compo Beach
Westport Uncorked | Oct | Longshore Inn
WINTER
Candlelight Concert | Dec | Staples HS
Menorah Lighting | Dec | Post Rd & Main St
Orphenians Concert | Dec | Downtown
Parents Night Out by DMA | Feb | Downtown Restaurant Partners
Monte Carlo Masquerade | Feb | Westport Museum for History & Culture
Temple Israel Polar Plunge | Jan. 1 | Compo Beach
WESTON EVENTS
Town Events | Weston
Lechat Town Farm | Tai Chi, Women’s Tea Party, Easter Egg Hunt, Summer Camps | Mar-Oct | 106 Godfrey Rd W, Weston
Memorial Day Fair | May | Hurlbutt Elementary School
Norfield Grange Fair | Sept | 12 Good Hill Rd
