Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of June!

Connect with fellow business and community members while learning more about business resources, marketing opportunities, and economic development initiatives from the City of Highland Park Business Development Team. Don’t miss this final First Wednesday before our summer break — we’ll return in August!

Date: Wednesday, June 3, 2026
Time: 7:30 - 9:00 AM
Location: Bluegrass, 1636 Old Deerfield Rd 

Register today to reserve your spot!

*Chamber members and non-members are welcome!

Join us on June 11 at 3 pm as we celebrate Big Frog North Shore with a ribbon cutting!

Hosted by DBR Chamber of Commerce, join us and other neighboring chambers and community members as we celebrate Big Frog Custom T-Shirts & More of North Shore. 

Big Frog North Shore creates custom apparel, branded merchandise, promotional products, team gear, and printing solutions for businesses, schools, nonprofits, and community organizations across the North Shore.

The afternoon will include:

• Ribbon-cutting ceremony

• Photos and video

• Tours of the space

• Networking and casual conversation

• Light refreshments

Event Schedule:
3:00 PM – Arrival + networking
3:15 PM – Ribbon-cutting ceremony
3:20–4:00 PM – Tours and conversation

All members of the community are welcome!

Highland Park Wine Stroll

Sip. Shop. Stroll. Savor.

Presented by the Highland Park Chamber of Commerce

While general participation registration has closed, there are still meaningful ways to be involved in the Highland Park Wine Stroll!

Businesses can now participate as a Take-Home Sponsor and/or Bag Sponsor, with their brand featured in the official event swag bags distributed to attendees. This is a great way to maintain visibility and engage with event guests even after the participation deadline. Click on the 'Register' button to check-out the current sponsorship opportunities.

In addition, we are also welcoming event volunteers to help support day-of logistics and guest experience. ------> Sign up here to volunteer!

This is a valuable opportunity to stay connected to one of Highland Park’s most highly attended events and still benefit from event exposure and community engagement.
 

Be a part of one of Highland Park’s most anticipated community events! The Highland Park Wine Stroll draws residents and visitors alike to our vibrant downtown for an evening of wine tastings, shopping, and fun! You’ll have the unique opportunity to showcase your brand and products and/or services and connect with new customers in a fun, social setting.

Event Details:

Date: Thursday, June 18, 2026
Time: 5:00 PM - 7:30 PM CST
Location: Downtown Highland Park, IL

Who Should Participate:

Retail | Galleries | Restaurants | Salons/Spas | Professional/Service Businesses

​Feeling collaborative? Any Highland Park business can participate! Whether you're downtown or elsewhere in the community, there’s room for you. Partner with a downtown brick-and-mortar to elevate the guest experience, reach new customers, and showcase your business as an engaged, community-minded brand. It’s a smart way to cross-promote, build visibility, and be part of the energy.

Why Participate:

• Drive additional sales by staying open later and converting high foot traffic into same-day purchases.
• Attract new customers and introduce your business to 100+ engaged event-goers.
• Increase visibility and brand awareness through inclusion on the official event map, signage, and Chamber marketing promotions.
• Create meaningful engagement with curated wine samples (or non-alcoholic option)
• Incentivize purchases and repeat visits with exclusive event-day specials, raffles, or samples.
• Leverage Chamber marketing support through social media and digital promotions to extend your reach beyond event night.

IMPORTANT REGISTRATION DETAILS:

Please note: Businesses registering after April 20 are not guaranteed inclusion in all marketing and promotional materials.

Participation Fees:

Highland Park Chamber Members: $150.00
Non-Chamber Members: $250.00

Basic Requirements:

• Open and staffed during event hours
• Provide a space for wine tasting
• Collaborate with the Chamber wine partner

Sponsorship Opportunities

Sponsoring the Highland Park Wine Stroll is a toast-worthy opportunity to showcase your brand to a lively, engaged audience while supporting our local business community. Sponsors enjoy prominent recognition in event marketing, signage, social media, and press coverage, as well as valuable visibility in front of a hundred attendees. It’s a perfect way to align your business with a fun-filled event and make a lasting impression.

Check out sponsorship opportunities here.

Reach out to Michelle Friedman at michelle@chamberhp.com or (847) 432-0284 to talk about your sponsorship opportunity!

Our First Wednesday Connections series will take the month off, and we look forward to welcoming everyone back at our next gathering.

Highland Park Sidewalk Sale 2026

July 24–25 | 10 AM – 5 PM | Downtown Highland Park

Secure Your Spot Today

Be part of Highland Park’s biggest shopping event of the summer. For two high-traffic days, the Central Business District transforms into a vibrant, open-air marketplace filled with shoppers ready to discover, browse, and buy.

This is your opportunity to get your business front and center in one of the North Shore’s most anticipated summer traditions.

Why You Can’t Miss This

• Reach a high-volume mix of local residents and regional visitors
• Drive immediate sales and long-term customer relationships
• Increase visibility for your brand in a prime downtown setting
• Be part of a lively, high-energy shopping experience

Who Should Participate

Retailers | Artists | Pop-Ups | Restaurants | Service Providers | Nonprofits

Chamber members, local businesses, and vendors from surrounding communities are all welcome.

What You Get

• Assigned sidewalk space in a high-traffic area
• Multi-channel event promotion (email, social, print)
• On-site support from the Chamber team
• Access to thousands of engaged shoppers

Key Details (Read Before Registering)

• All vendors are limited to a 10x10 space (or equivalent)
• Placement is assigned based on vendor setup and sidewalk capacity to maximize traffic flow and overall experience
• Vendor mix is curated to ensure variety (similar businesses will be spaced apart)
• Chamber Members receive priority placement
• Vendors must provide their own tents, tables, and displays

Deadline: June 16, 11:59 PM CST

Claim Your Spot Now

Click the “Register” button above to secure your space - don't wait!

Questions?

View the Vendor Handbook (Rules, FAQs, & Tips) here.

For sponsorship opportunities, contact Michelle Friedman at michelle@chamberhp.com or 847-432-0284.

Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of August!

*Chamber members and non-members are welcome!

Join us for an evening of networking and connection at our First Wednesday Connections event in the month of September!

Stay tuned for more information.

*Chamber members and non-members are welcome!

Join us for a morning of networking and breakfast at our First Wednesday Connections event in the month of October!

*Chamber members and non-members are welcome!

Join us for an evening of networking and connection at our First Wednesday Connections event in the month of November!

Stay tuned for more information.

*Chamber members and non-members are welcome!

First Wednesday Connections will take a brief pause this month as we celebrate the holiday season. We look forward to seeing you at our Holiday Celebration on December 10th.

Celebrate the Season with the Highland Park Chamber of Commerce!

Get ready to enjoy festive bites, seasonal sips, and the company of friends old and new at the beautiful Summer Classics Home. We'll raise a glass to another year of thriving local businesses, meaningful connections, and shared successes.