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  • Holiday Stroll Holiday Stroll

    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!

    RSVP here for Photos with Santa at Wildwood Photography! You must RSVP to reserve your photo session with Santa by registering for one of four 30-minute time slots from 5-7PM during the Southport Holiday Stroll & Cocktail Crawl. Space is limited!

    RSVP to the Southport Holiday Stroll & Cocktail Crawl event on Facebook!

  • Cocktail Crawl Cocktail Crawl

    This year, we are expanding the Southport Holiday Stroll to include a ticketed Cocktail Crawl. For the Cocktail Crawl, attendees can sample 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 cocktails and participating business locations, as well as the cocktail samples along the crawl. The Cocktail Crawl check-in location is at Lakeview Chamber office (1409 W. Addison St) from 4:30pm - 7:00pm.

  • Thank You To Our Event Partners! Thank You To Our Event Partners!


  • Event Details Event Details

    Friday, December 7, 2018
    5:00pm - 9:00pm

    Holiday Stroll

    • FREE (No Ticket Required) 

    Cocktail Crawl

    • $25 early bird
    • $30 in advance
    • $40 day of event


    *The Cocktail Crawl is a rain or shine event.  All ticket-holders must be of legal drinking age.  ID’s will be checked at time of registration.
    **All tastings take place within the businesses listed on the ticketed route.  Cocktail pours are offered in 2 ounce tasting portions at each business.  Over 15 different cocktails will be available to taste along the crawl.  Businesses listed on the crawl are subject to change.