Crowds gather downtown at the 2025 Holiday Stroll
Brought to you by Westport Downtown Association logo in collaboration with 06880 logo
Saturday, December 54 to 7 PM

The Sixth Annual

Holiday
Stroll

An evening of holiday shopping, dining and music in downtown Westport. Browse this year's promotions below and plan your route.

Date
Sat, Dec 5
Time
4 to 7 PM
Where
Downtown
Browse Promotions Businesses: Submit Your Promotion Holiday Stroll Map Coming Soon

At the Elm + Main Lot

Holiday vendors in the Elm + Main Lot
Holiday Vendors

To be announced.

Live music at the Holiday Stroll
Live Music

To be announced.

Holiday characters greeting families
More to Come

Coming soon.

A special thank you to Aubuchon Realty Company, Inc. (ARC) for generously providing the Elm + Main Lot to our community every year.

Vendor Spaces Available During the Event

Bring Your Business Downtown

Vendor spaces are available in two locations: Main Street and the Elm + Main Lot. Availability is limited and offered first come, first served. WDA members receive a discounted rate.

WDA Members
$300
Non-Members
$400
Food Vendors
$350

To reserve a space, contact Rachel Katzman, Events Director, at events@westportdowntown.com.

Inquire About Vendor Space

With Thanks to Our Sponsors

Main Sponsors
BMW of Bridgeport logo Savvy + Grace logo
In-Kind Sponsors
Dan Woog's 06880 logo Aubuchon Realty Company, Inc. logo Awesnap logo Whimsy Works Atelier logo

The Promotions Guide

Submit Your Promotion
Business
Promotion Details
Promotion Period
Loading promotions...

Scenes from Last Year

The downtown clock and holiday tree at dusk
Roasting s'mores by the fire pit
A family enjoying the Stroll
Festive shoppers on Main Street
Decorated storefronts downtown
Photos from the 2025 Holiday Stroll by Dave Robbins Photography
Attention Westport Businesses

Share Your Holiday Promotion

Retailers, restaurants and service businesses are invited to take part. Every promotion is featured here and on 06880. Free to participate.

  • Submit your promotion complete and final.
  • Promotions will be posted exactly as submitted.
  • Offered only to Westport based businesses, including e-commerce businesses with a Westport address.

Deadline: Wednesday, December 2, at 3 PM

Submit Your Promotion
See you downtown, Westport.
Hosted by the Westport Downtown Association + Dan Woog's 06880
Back to Top ↑