2024 Annual Southport Holiday Stroll and Cocktail Crawl Details

It’s that time of year again for the Lakeview Roscoe Village Holiday Stroll and Cocktail Crawl!

Southport Holiday Stroll & Cocktail Crawl
December 6, 5 PM – 9 PM

Celebrate the season with holiday decorations, festive carolers, photos with Santa, delicious holiday cocktails, tasty treats, special offers, and more!

Get Your Tickets Now!

Check-In Locations for Ticket Holders
(Available for check-in from 4:30 PM – 7:30 PM on the day of the event)

Route A: Addison to Irving Park Rd
Check-in at the Chamber Office, 1409 W. Addison St.
Route B: Belmont to Addison
Check-in at Sheil Park, 3505 N. Southport Ave.

Ticketed Cocktail Crawl
Join the Cocktail Crawl and explore two festive routes, each featuring 10+ holiday-themed cocktails. While you sip and stroll, enjoy the Southport Holiday Stroll’s seasonal charm and shop local stores for unique gifts!

Your Cocktail Crawl ticket includes:

A commemorative tasting glass
An event guide with a list of participating stops
Tastings of delicious holiday-themed cocktails

Route A Businesses (Irving Park to Addison)

Mahogany Builders: 3823 N Southport Ave
Steingolds of Chicago: 3737 Southport Ave
Candyality: 3737 N Southport Ave
312 Estates: 3753 N Southport Ave
Music Box Lounge & Garden: 3733 N Southport Ave
Dona Tola: 3751 N Southport Ave
BabyDolls Boutique: 3717 N Southport Ave
Click Shoes & More: 3729 N Southport Ave

Route B Businesses (Addison to Belmont)

Denim Lounge For Men: 3544 N Southport Ave
Galleria Liqueurs-Southport: 3409 N Southport Ave
Kendra Scott: 3426 N Southport Ave
Crosby’s: 3455 N Southport Ave
Tuco & Blondie: 3358 N Southport Ave
Konbini and Kanpai: 1433 W Belmont, Unit 1
Arc’teryx: 3441 N Southport Ave
Itoko: 3325 N Southport Ave
Framebridge: 3453 N Southport Ave
Little Goat Diner: 3325 N Southport Ave

About the Southport Holiday Stroll
A cherished tradition in West Lakeview, the Southport Holiday Stroll invites you to shop local, enjoy seasonal festivities, and get into the holiday spirit! The stroll is free to attend, with special deals, carolers, photos with Santa, holiday treats, and more festive surprises from local businesses.

Don’t miss this magical evening of holiday fun!