Events Calendar
HIGHLAND PARK WINE STROLL 2026
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.
YOUNG PROFESSIONALS GROUP PAINT & SIP
Join the Young Professionals Group for a special Paint & Sip evening on Thursday, June 25, from 4:30–6:30 PM at Braeside Market (55 St. Johns Ave)! This fun, impromptu gathering came together thanks to the generous support of our event sponsors—Braeside Market, The Custom Framer of Highland Park, and First Bank of Highland Park—and we're excited to bring young professionals together for an evening of creativity, connection, and community. Whether you're looking to expand your network, meet new people, or simply unwind after work, you'll enjoy a guided painting experience in a relaxed and welcoming atmosphere. Light bites, wine, and non-alcoholic beverages will be provided—just bring yourself and get ready to create, sip, and socialize. Space is limited, so register today and secure your seat at the canvas!
JULY FIRST WEDNESDAY CONNECTIONS 2026
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
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.
