Enjoy holiday decorations, carolers, photos with Santa, holiday-themed cocktails, treats, special offers & other festivities!

The Southport Holiday Stroll is a longstanding tradition in West Lakeview where break out the holly and stay open late offering special holiday deals and festivities. The Southport Holiday Stroll is free to attend and includes special deals from local businesses, carol singers, photos with Santa, holiday treats, and other surprises!

You can choose between two routes for the ticketed Cocktail Crawl and taste 10 different holiday-themed cocktails on your route while you enjoy the festivities of the Southport Holiday Stroll and shop for gifts at local stores!

The Cocktail Crawl ticket includes a commemorative tasting glass, event guide listing stops along the route, and tastings of the holiday-themed cocktails. Purchase here.