Southport’s Holiday Stroll details for Friday, December 3, 2021

The Southport Holiday Stroll & Cocktail Crawl on Friday, Dec. 3 from 5-9pm at businesses along Southport Avenue from Belmont to Irving Park Road!

Enjoy holiday shopping at local businesses, special discounts, carolers, Santa, holiday-themed cocktails and more festivities!

The Southport Holiday Stroll is free to attend, and you can purchase a ticket for the Cocktail Crawl to taste 10 holiday-themed cocktails along one of two routes while you enjoy the festivities of the stroll!

Find business discounts and learn more at https://www.lakeviewroscoevillage.org/southporthscc

Southport’s Annual Holiday Cocktail Crawl is Friday, December 6, 2019

It’s that time of year again so get your tickets here! 

From the Lakeview Chamber of Commerce:

  • 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!
  • Cocktail Crawl

    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.

Southport’s Annual Holiday Stroll is Friday, December 7, 2018 at 5 PM – 9 PM

It’s that time of year again!

Here are all the details from the Lakeview Chamber of Commerce via Facebook:

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!

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.

Find details about participating businesses at LakeviewChamber.com/HolidayStroll

RSVP at LakeviewChamber.com/HolidayStroll for a time slot to take Photos with Santa at Wildwood Photography from 5-7PM during the Southport Holiday Stroll & Cocktail Crawl!

This event is sponsored by Deep Eddy VodkaLarceny Bourbon and Green Mountain Energy Company.

The 22nd Annual Southport Holiday Stroll is December 1, 2017

It’s that time of year again! The Southport Holiday Stroll will be held on Friday, December 1, 2017 from 5:00 PM – 9:00 PM this year from Belmont to Irving Park Road. More information can be found here from the Lakeview Chamber of Commerce!

The Southport Holiday Stroll is December 2, 2016

It\’s that time of year again!  The annual Southport Holiday Stroll will be held on December 2, 2016 from 5:00 PM – 9:00 PM on Southport Avenue from Belmont to Irving Park Road. More information can be found here from the Lakeview Chamber of Commerce.

Continue reading “The Southport Holiday Stroll is December 2, 2016”

The 2015 Southport Holiday Stroll is Friday, December 4

It’s that time of year again!  The Southport Holiday Stroll will be Friday, December 4, 2015 – 5PM – 9PM from Belmont to Irving Park Road along Southport Avenue.  Jollypalooza will be on Saturday, December 5 on Lincoln Avenue.  More information from the Chamber of Commerce can be found here.

Southport’s Annual Holiday Stroll: Friday, December 5, 2014

It\’s that time of year again!  Southport’s Annual Holiday Stroll will be on Friday, December 5, 2014 from 5:00 – 9:00 PM from Belmont to Irving Park on Southport Avenue.  More details from the chamber can be found here!

Southport Corridor Holiday Stroll is December 6, 2013

Hard to believe the holidays are so close!Name: Southport Holiday Stroll
Date: December 6, 2013
Time: 5:00 PM – 8:00 PM
Event Description: It’s time for our Annual Southport Holiday Stroll!

Bring the family and enjoy festive lights, carolers, Santa & Mrs. Claus and plenty of holiday cheer.
Plus, participating Southport businesses will be open late and offering refreshments and shopping incentives!


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