The Southport Holiday Stroll is a longstanding tradition in West Lakeview where businesses along Southport between Belmont and Irving Park 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!
For the Cocktail Crawl, attendees can taste over 15 different holiday-themed cocktails at participating businesses while they enjoy the festivities of the Southport Holiday Stroll. All businesses participating in the Cocktail Crawl are also part of the Southport Holiday Stroll.
With a Cocktail Crawl ticket, each cocktail taster will receive a commemorative tasting glass and map guide listing the participating businesses and various cocktails. The Cocktail Crawl Check-In location is at Sheil Park (3505 N. Southport Ave) from 4:30 - 7:30pm.