Westport CALENDAR

The calendar year is full in Westport with art and craft shows, blues festivals, free outdoor music and summer fireworks. Below is a taster 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
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

Tuesdays @ the Train | June-Aug | Luciano Park 

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 

Blues, Views & BBQ Fest | Sept | Levitt Pavilion 

ChowdaFest | Oct | TBD

Christmas Tree Lighting | Nov/Dec | Town Hall

CLASP Homes Benefit | Oct | TBD

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 

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 | Imperial Parking Lot 

Westoberfest | Oct | Elm Street 

Westport Kiwanis Club Triathlon | Sept | Compo Beach

Westport Uncorked | Oct | Longshore Inn 

WINTER

Candlelight Concert | Dec | Staples HS

Holly Days by Westport Historical Society | Nov/Dec | Downtown

Horse & Carriage & Family Day w/ Santa | Dec | Historical Society

Menorah Lighting | Dec | Post Rd & Main St 

MOCA Winter Outdoor Lights Festival | Feb. 27 | 19 Newtown Tpk 

Orphenians Concert | Dec | Downtown

Parents Night Out by DMA | Feb | Downtown Restaurant Partners

Temple Israel Polar Plunge | Jan. 1 | Compo Beach

Vintage Valentine’s Day Cupid Kit | Feb | Westport Historical Society, 25 Avery Pl

WESTON EVENTS