Southport Holiday Stroll and Cocktail Crawl – Sip Stroll Along Southport Ave!

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About this event:

Get in the holiday spirit by tasting 10 different holiday-themed cocktails at participating businesses along Southport Ave while you shop the Southport Holiday Stroll! This ticketed Cocktail Crawl features two routes and takes place alongside the festivities of the Southport Holiday Stroll. The Southport Holiday Stroll is free to attend and includes special deals from local businesses, carolers, photos with Santa, holiday treats, and other surprises.

Cocktail Carolers

When and where:

Fri, December 2, 2022, 5:00 PM – 9:00 PM CST


Southport Ave from Belmont to Irving Park Rd 3505 N Southport Ave Chicago, IL 60657

Route A includes businesses along Southport Ave from Addison to Irving Park and Route B includes businesses along Southport Ave from Belmont to Addison. You are welcome to visit businesses on the opposite route as part of the Southport Holiday Stroll, but you will only be able to receive cocktail tastings at the businesses along your ticketed route.

A limited number of early-bird tickets are on-sale for $25 while supplies last. General admission tickets are $40.

Each Cocktail Taster will receive a commemorative tasting glass, cocktail samples on either Route A or Route B along the stroll, and an event guide listing the cocktails and business locations.

The cocktail crawl is a great way to support local and small businesses

Check-in Locations for Ticket Holders (Check-in is from 4:30pm – 7:30pm day of the event):

Route A: Addison to Irving Park Rd – Check in at Chamber Office, 1409 W. Addison St

Stops on this route include:

Port and Park Bistro and Bar

Mahogany Builders

312 Estates

Dona Tola

Batik Chicago

Steingold’s of Chicago

Music Box Lounge & Garden

BabyDolls Boutique

The Guild

Cafe Tola

Suvarna Chiropractic with YogaSix


Mercury Theatre

Click Shoes

Route B: Belmont to Addison – Check in at Sheil Park, 3505 N. Southport Ave

Stops on this route include:

The Butcher’s Tap

The Denim Lounge for Men


Corridor Brewery & Provisions

Kendra Scott

AURA Candle Bar with Bitter Pops

Konbini & Kanpai

Crosby’s Kitchen

Tuco and Blondie

Galleria Liqueurs-Southport

Big City Optical

*This 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 each ticketed route. Cocktail pours are offered in 2 ounce tasting portions at each business. 10 different cocktails will be available to taste along each route. Businesses listed on each route are subject to change.

Thank you to the event partner, Garfield’s Beverage!


To purchase tickets, visit the Lakeview Village Roscoe website.


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