Frankfort Wine & Ale Walk: An Afternoon on the Green | Weekend Guide
Adults with tasting glasses strolling a historic downtown street with shops and a live band on the green
Illinois · Dining & Drinks ·

Frankfort Wine & Ale Walk: An Afternoon on the Green

Frankfort's 14th Annual Wine & Ale Walk returns Sunday, Sept 27, 2026, from 2 to 6 p.m., with tastings at downtown businesses and live music on the Breidert Green stage.

Frankfort's 14th Annual Wine & Ale Walk is set for Sunday, Sept 27, 2026, from 2 to 6 p.m. in the historic downtown. It is a 21-and-older event where ticketholders stroll the brick sidewalks, sampling wines and ales alongside appetizers and desserts at participating shops and restaurants, with live music on the Breidert Green stage. It is a relaxed, grown-up way to spend a late-September afternoon and a chance to see downtown Frankfort at its liveliest. Tickets went on sale in early August and the walk tends to sell out, so grab yours ahead of time and plan to wander the boutiques between stops.

Spots to Check Out

Wine & Ale Walk

Sunday, Sept 27, 2 to 6 p.m., a 21-and-older stroll through historic downtown Frankfort with wine and ale samples, appetizers, and desserts at local businesses.

Breidert Green

The historic downtown park where live entertainment sets up on the stage during the walk.

Downtown Frankfort

Make an afternoon of it: explore the boutiques and bakeries between tasting stops.

Joanne Dal Santo

Curated By

Joanne Dal Santo

Associate Broker, @properties · Your local insider for Chicagoland and Northwest Indiana weekends.