Sidewalk Sale
Jul
7
Jul 9

Sidewalk Sale

The much-anticipated annual Westport Sidewalk Sale allows savvy shoppers to find amazing sales throughout Main Street, Post Road and areas surrounding downtown. Shops bring merchandise to the sidewalks and offer incredible bargains. Times will vary by store, but shop early for the best selection!

Westport Fine Arts Festival
Jul
15
Jul 16

Westport Fine Arts Festival

Now in its 44th year, the Westport Fine Arts Festival remains a highlight on the calendars of art collectors from New England and Manhattan each year.

Blues Views & BBQ
Sep
2
Sep 3

Blues Views & BBQ

  • LEVITT PAVILION & WESTPORT LIBRARY GROUNDS

Celebrating its 10th year, the Westport Downtown Merchants Association hosts  a foot stomping, mouth watering weekend of great music, food and activities for children and adults.

Westport Fashion & Beauty Week
Oct
16
Oct 20

Westport Fashion & Beauty Week

  • Main Street Westport, CT, 06880 United States

New to downtown this year, the WDMA and our merchants will host a week of fashion and beauty events, trunk shows and demonstrations.   More details coming soon!


Santa Visits Downtown
Dec
22
3:00 pm15:00

Santa Visits Downtown

A true crowd pleaser for young and old, Santa will be visiting downtown 5 days throughout the holiday season. On the 13th and the 20th he will give his reindeer the day off and hitch a ride downtown with the Westport Fire Department on one of their shiny red trucks.

Horse and Wagon
Dec
22
3:00 pm15:00

Horse and Wagon

Back by popular demand, Horse and Wagon rides will be available on December 22nd from 3-6pm. The pick up location will be in front of Bedford Square on Church Lane (across from Pink Sumo Sushi).

Fire Truck Santa
Dec
20
4:00 pm16:00

Fire Truck Santa

Santa will arrive on the fire truck at the corner of Avery Place and Main Street at 4pm. Enjoy music by Acoustic Dizzy Fish, as well as plenty of opportunity for photos.

Santa Visits Downtown
Dec
17
12:00 pm12:00

Santa Visits Downtown

A true crowd pleaser for young and old, Santa will be visiting downtown 5 days throughout the holiday season. On the 13th and the 20th he will give his reindeer the day off and hitch a ride downtown with the Westport Fire Department on one of their shiny red trucks.

Fire Truck Santa
Dec
13
4:00 pm16:00

Fire Truck Santa

  • Paper Source Pation

Meet Santa and his fire truck escort at the Paper Source and Steven Alan Patio at 4 pm.  Enjoy music by Acoustic Dizzy Fish and Paper Source will offer a “Make and Take” holiday craft for $8.

Santa Visits Downtown
Dec
11
2:00 pm14:00

Santa Visits Downtown

A true crowd pleaser for young and old, Santa will be visiting downtown 5 days throughout the holiday season. On the 13th and the 20th he will give his reindeer the day off and hitch a ride downtown with the Westport Fire Department on one of their shiny red trucks.

Seasonal Music
Nov
25
Nov 26

Seasonal Music

Enjoy the sounds of the season as you walk, shop and dine around downtown on various days throughout the holiday season.

Seasonal Valet Parking
Nov
25
Dec 24

Seasonal Valet Parking

Park your sled with us!

$5 per vehicle

Seasonal valet parking in downtown Westport begins on Black Friday, November 25, 2017 and runs weekends through December 24th, including Friday, December 23.