Highland Park Wine Stroll 2026
About this Event
Highland Park Wine Stroll
Sip. Shop. Stroll. Savor.
Presented by the Highland Park Chamber of Commerce
Join us for an unforgettable evening in downtown Highland Park as we blend community charm with wine-filled fun at our Highland Park Wine Stroll!
Stroll through our vibrant downtown district while enjoying delicious wine tastings at a curated selection of local businesses. Whether you're looking to discover a new favorite wine, find a one-of-a-kind gift, or simply enjoy a festive night out, this event is for you!
Event Details
- Date: Thursday, June 18, 2026
- Time: 5:00 PM - 7:30 PM CST (VIP begins at 4:30 PM CST)
- Check-in Location: First Bank of Highland Park, 1835 1st Street (Check-in is available from 5 PM until 5:45 PM)
NEW THIS YEAR: VIP Wine Experience (Limited - 20 Tickets)
Upgrade your evening with an exclusive VIP experience.
Begin at 4:30 pm with a private outdoor wine tasting at Summer Classics Home, hosted by the winemakers from Lynfred Winery.
Enjoy:
- Curated wines not available during the main stroll
- Outdoor VIP setting with live music
- Light bites and a relaxed, elevated atmosphere
Only 20 VIP tickets are available!
What to Expect
- Stroll through downtown Highland Park's vibrant streets. Be sure to wear your walking shoes!
- Wine tastings from Highland Park's Vin Chicago and Lynfred Winery. Non-alcoholic beverages are available.
- Enjoy special in-store promotions, discounts, and product showcases, plus grab a swag bag at check-in
- Light bites and treats at select stops
- Fun photo ops and social media moments
Ticket Options
- VIP Ticket: $75 each (ONLY 20 TICKETS AVAILABLE)
- Single Ticket: $30 each
Participating Locations
Exclusive offerings for Wine Stroll participants from:
- Summer Classics Home - 40% discount on Summer Classics & Gabby items, 20% discount on accessories
- Lynfred Winery Highland Park - 20% off bottle purchases
- Ravinia Festival (located in Lynfred Winery Highland Park) - win fun prizes
- ABLAZE Design Group (at The Vault Creative) - FREE swag
- Zeifert Eye Care
- Local Leaf Farm - 25% off purchases
- Therapeutic Kneads - mini massages, mocktails, swag, & 20% off retail
- The Vault Creative
- Style Shack - 10% off
- Pets4Life - 20% off select retail
- The Art Center of Highland Park
- FACE FOUNDRIÉ - 50% off future bookings
- Gearhead Outfitters Highland Park - 20% off a full priced item
- The Custom Framer of Highland Park - 50% off art plus a themed-photo station
- Sunflower - 20% discount
- Rock N Rags
- & more!
Why You'll Love It
This isn’t just a wine tasting—it’s a full downtown experience.
Perfect for a date night, girls’ night out, or group outing, the Wine Stroll brings together the best of Highland Park’s shops, restaurants, and community energy in one walkable evening.
Every ticket supports local businesses and helps strengthen the heartbeat of Highland Park.
Check-in & Requirements
- Register on Eventbrite
- Check-in Opens: 5:00 PM at First Bank of Highland Park (1835 1st Street)
- ID Required: Must be 21+ to participate in wine tastings
Thank you Sponsors!
First Bank of Highland Park
Summer Classics Home - Chicago
Vin Chicago
Lynfred Winery Highland Park
The Custom Framer of Highland Park
Merel Family Law
Ravinia Festival
Life Rhythms
Questions?
Contact: Andrea Barattini
Marketing Manager, Highland Park Chamber of Commerce
847-432-0284.
Agenda
🕑: 04:30 PM
VIP Check-in
Host: Summer Classics Home
Info: VIP attendees will enjoy an exclusive wine tasting with Lynfred Winery winemakers. This pre-event concludes by 6 PM, after which VIP guests will join general admission attendees for the remainder of the Wine Stroll.
🕑: 05:00 PM - 05:45 PM
Check-in
Host: First Bank of Highland Park
Info: Check-in to receive your lanyard, wine glass, and event map. Your first wine tasting starts here!
🕑: 05:30 PM - 07:30 PM
Stroll, Shop, & Enjoy!
Info: Stroll the streets of downtown Highland Park and visit the participating businesses while sipping, shopping, and savoring! Maps and additional signage will be available.
Where is it happening?
Event Location & Nearby Stays:
USD 33.85 to USD 81.88
