111 North Ave

Celebrate Highwood is excited to announce its 2026 season of festivals and community events. The year begins with the Evening Gourmet Market (June 3–August 26), bringing weekly Wednesday nights of food, music, and more than 60 vendors to Everts Park. Summer officially kicks off with the Kick-off to Summer Carnival (June 5–7), followed by the fiery fun of Inferno Fest (June 24). July features Highwood Days &amp; the 2nd Annual Taste of Highwood (July 17–19), along with the community‑favorite Highwood 5K Run, Walk &amp; Stroll (July 18). Later in the month, Margarita Night (July 29) brings tropical energy and Jimmy Buffet–style entertainment. August highlights include Garlic Fest (August 12), celebrating creative sweet and savory garlic dishes, and Bloody Mary Fest (August 16), where mixologists showcase inventive tomato‑based cocktails. Over Labor Day weekend, Nashwood (September 4–6) transforms Downtown Highwood into a Nashville‑inspired music takeover. Fall brings the iconic Great Highwood Pumpkin Festival (October 2–4), the North Shore’s largest autumn celebration, and the year wraps up with the festive Elf Invasion Pub Crawl (December 5).

Local Event: Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

Lake County

Highland Park

Illinois

Celebrate Highwood Announces 2026 Series of...

Celebrate Highwood is excited to announce its 2026 season of festivals and community events. The year begins with the Evening...

Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

Celebrate Highwood’s Wednesday Evening Gourmet Market brings together great food, community spirit, and a lively mix of live music all season long. Guests can explore local flavors while enjoying performances from a rotating lineup of regional favorites. The atmosphere is upbeat and welcoming, with bands and DJs that keep the energy high throughout the evening. This year’s lineup features acts such as The Vibe Cruisers, Rollover Band, Roger Black Band, Red Funk Band, DJ Versace, and more, creating a vibrant soundtrack for one of Highwood’s most popular weekly traditions.

Local Event: Celebrate Highwood – Wednesday Evening Gourmet Market Music Lineup

Highwood

Celebrate Highwood – Wednesday Evening Gourmet...

Celebrate Highwood’s Wednesday Evening Gourmet Market brings together great food, community spirit, and a lively mix of live...

Celebrate Highwood – Wednesday Evening Gourmet Market Music Lineup

57th Street, Between Woodlawn and Kenwood Avenues Hyde Park, IL 60637

The 79th Annual 57th Street Art Fair returns June 6, 11 AM–6 PM, and Sunday, June 7, 10 AM–5 PM, featuring nearly 200 artists and thousands of original works! As the Midwest’s oldest juried art fair, this dedicated volunteer-run event is a must-visit for art lovers looking to shop, discover, and connect with artists from across the country.

Guests can browse a wide range of handmade items, including jewelry, glass, ceramics, paintings, sculptures, fiber art, leather goods, photography, and more. Enjoy live music from Buddy Guy’s Legends, family-friendly activities, and food trucks serving up delicious bites—all while chatting with artists about their creative process!

All works are juried and original, continuing the vision of founder Mary Louise Womer from 1948, with artists receiving full monetary benefit from their sales.

For more information, visit: <a href="https://www.57thstreetartfair.org " rel="nofollow" target="_blank">https://www.57thstreetartfair....</a>;

Local Event: The 79th Annual 57th Street Art Fair: June 6–7, 2026

Cook County

Hyde Park

The 79th Annual 57th Street Art Fair: June 6–7,...

The 79th Annual 57th Street Art Fair returns June 6, 11 AM–6 PM, and Sunday, June 7, 10 AM–5 PM, featuring nearly 200 artists...

The 79th Annual 57th Street Art Fair: June 6–7, 2026

57th Street, Between Woodlawn and Kenwood Avenues Hyde Park, IL 60637 IL

Celebrate Highwood invites the public “show their pride on the North Side” as they host Pride in the Park, a celebration of love and community, on Wednesday, June 17 from 4:30 - 9 PM. This new theme night during the beloved weekly Evening Gourmet Market will focus on family-friendly inclusivity, loaded with interactive art, games, and live entertainment by Highwood’s own DJ Versage, who’s high energy is as fun to watch as they are to listen to, playing hits for the whole family. For those looking to leave a lasting mark, Pride in the Park will feature an interactive mural installation, courtesy of The Art Center Highland Park. The ‘Find your Piece of the Puzzle’ community mural invites attendees to paint and collaborate on a puzzle piece that will be transformed into next year’s annual Pride in the Park poster. A Celebrate Highwood ‘Pride Rocks Garden’ painting station hosted by the North Shore Civic Club will offer guests the opportunity to paint custom rocks to be displayed in the community. Free activity tables will be onsite, as well as giant yard games to play, including Connect 4, Jenga, and Twister.

Local Event: Pride in the Park

Pride in the Park

Celebrate Highwood invites the public “show their pride on the North Side” as they host Pride in the Park, a celebration of...

Highland Park just announced its biggest EnjoyHP season yet, running June–October 2026. The expanded lineup features free, family‑friendly festivals, concerts, and community events that have already drawn more than 80,000 visitors since 2022.
2026 highlights include: 
• Taste of Highland Park (June 19–20): More restaurants, more music, air‑conditioned lounges, a photo exhibit, and expanded kids’ programming.
• Downtown Concert Series (Fridays, July 10–Sept. 25): Free concerts with global cuisine, world music themes, and the return of the Scarecrow Trail.
• Vintage Car Show (Aug. 22): A larger footprint plus an all‑new electric vehicle showcase.
• Oktoberfest (Sept. 26): Bavarian music, beer &amp; bites, stein‑holding, axe throwing, and family fun.
• Stews &amp; Brews (Oct. 10): Comfort foods, craft beverages, fire pits, kids’ activities, and the People’s Choice competition.
Highland Park is gearing up for its most engaging, diverse season yet. Here is a link to past events too!

Local Event: Highland Park Announces 2026 EnjoyHP Lineup

Highland Park Announces 2026 EnjoyHP Lineup

Highland Park just announced its biggest EnjoyHP season yet, running June–October 2026. The expanded lineup features free,...

Central Avenue, between Second St. and St. Johns Ave., and in Port Clinton Square (600 Central Ave.

Two days. Live music. Local flavors. Family fun. Taste of Highland Park is back June 19–20 with headliners All American Throwbacks (Friday) and Eve 6 (Saturday), plus performances from Highland Park Players, ALATS Dance Company, Mike &amp; Joe, Laura Doherty, and more. Enjoy extended Saturday hours, kids’ programming, climate‑controlled dining, and bites from 12+ Highland Park restaurants. Your summer weekend starts here.

Local Event: Taste of Highland Park Returns June 19–20!

Taste of Highland Park Returns June 19–20!

Two days. Live music. Local flavors. Family fun. Taste of Highland Park is back June 19–20 with headliners All American...

Sheridan Road & Clay Avenue

The public is invited to put on their sneakers, grab their family, friends, strollers, and pets and join the fun on Saturday, July 18 at 9 AM in Downtown Highwood. The course starts and finishes at the corner of Sheridan Rd &amp; Clay Ave. and will guide participants along the beautiful lake front trail and through historic Fort Sheridan and then back again. This year’s run embraces a special "Superhero" theme, encouraging participants to come dressed as their favorite superhero. “Celebrate Highwood is thrilled to partner with Oak Terrace and align with their ‘Be a Superhero in Your Community’ theme,” says Celebrate Highwood president, Jess Ortega. “Oak Terrace’s platform on community mindedness goes hand in hand with our mission with Celebrate Highwood!”
Proceeds from the 2026 Celebrate Highwood 5K will directly benefit the Oak Terrace PTO, a non-profit organization committed to developing closer connections between home and school.
Runners and walkers can sign up <a href="https://www.CelebrateHighwood.org" rel="nofollow noopener" target="_blank">HERE</a>&nbsp;or at www.CelebrateHighwood.org now through midnight on Saturday, July 18. The 5K Run, Walk &amp; Stroll registration fee is $45 per participant, and includes a run t-shirt (must be registered by Monday, July 6 to guarantee a shirt and size). The one-mile walk fee is $25 and does not include a t-shirt. Participants aged 21 and older, will receive a coupon for an alcoholic beverage to enjoy at the Celebrate Highwood bar located at the Taste of Highwood in Everts Park, or the Celebrate Highwood bar at Highwood Days, held at the Highwood Metra Station parking lot, through Sunday, July 19.
Race Day Schedule &amp; Logistics: 8:00 AM: Race Day Registration and Packet Pick Up opens (Intersection of Sheridan Rd &amp; Clay Ave) 9:00 AM: 5K Race Start 10:00 AM: Age Group Awards Ceremony (or when the last participant crosses the finish line)
Age Group Awards: Celebrate Highwood will recognize the 1st, 2nd, and 3rd place Male and Female finishers in two age groups: 16 &amp; under, and 17 &amp; over.

Local Event: Highwood 5K Family Run, Walk & Stroll

Highwood 5K Family Run, Walk & Stroll

The public is invited to put on their sneakers, grab their family, friends, strollers, and pets and join the fun on Saturday,...

info

Rachel Barnes

Chicago Metropolitan Area

Eric DeGrechie

Deerfield

Northbrook

Winnetka-Glencoe

Lake Forest-Lake Bluff

Glenview

Buffalo Grove

Vernon Hills

Wilmette-Kenilworth

Niles-Morton Grove

Amie Schaenzer

Libertyville

Friday, May 15 9:30am-3:30pm (numbers @9)Saturday, May 16 10:00am-3:00pmParking on Hawthorne and Ravine is PERMITTED for this eventJoin us for this incredible authentic MCM sale in a historic home in Highland Park - wall to wall vintage treasures!
<ul><li>Fabulous period furnishings and original art, decor, and more.</li><li>Women's clothing, shoes and jewelry</li><li>Fully stocked kitchen</li><li>Vintage garden decor</li></ul>



MORE!!!Cash, Credit Cards, Zelle and Venmo accepted

Local Event: ReHOME Estate Sale in Highland Park

ReHOME Estate Sale in Highland Park

Friday, May 15 9:30am-3:30pm (numbers @9)Saturday, May 16 10:00am-3:00pmParking on Hawthorne and Ravine is PERMITTED for this...

Northbrook Village Green Park Center, 1810 Walters Avenue, Northbrook 60062

Gardeners:&nbsp;Shop 1,000’s of beautiful, well-behaved homegrown + nursery grown native plants, cultivars and favorites from our gardens to yours. Master gardeners available for gardening tips in our rain resistant indoor location. Email questions to info@northbrookgardenclub.org.

Local Event: Northbrook Garden Club Plant Sale Fri 5/15 (9-4) & Sat 5/16 (9-2)

Northbrook Garden Club Plant Sale Fri 5/15...

Gardeners: Shop 1,000’s of beautiful, well-behaved homegrown + nursery grown native plants, cultivars and favorites from our...

Northbrook Garden Club Plant Sale Fri 5/15 (9-4) & Sat 5/16 (9-2)

Deerfield Italian Kitchen

Come hang out with like minded people and see some beautiful nature photography at our next Deerfield Green Drinks. &nbsp;The speaker is a local nature photographer, Lisa Musgrave. &nbsp;The presentation title is - Slow down and look close! &nbsp;Come see photos of critters found in our forest preserves!
Food and drinks available for purchase.

Local Event: Green Drinks - Come see nature photography!  Speaker - Lisa Musgrave

Green Drinks - Come see nature photography! ...

Come hang out with like minded people and see some beautiful nature photography at our next Deerfield Green Drinks.  The...

Green Drinks - Come see nature photography!  Speaker - Lisa Musgrave

ObituaryMaurice Irwin &ldquo;Win&rdquo; Gould, Jr.
Maurice Irwin &ldquo;Win&rdquo; Gould, Jr., of Punta Gorda, Florida, formerly of Lake Bluff, Illinois, and native of East Aurora, New York, passed away peacefully in his sleep on May 13, 2026.
Win was a devoted husband, father, grandfather and lifelong maker. He was predeceased by his wife, Marilyn, and his beloved dog, Molly. He is lovingly remembered by his children Tom, Todd, and Betsy, and by many grandchildren who brought him great joy.
A meticulous craftsman, Win found deep satisfaction in building architectural models and intricate ship models, and he spent countless hours painting and restoring classic automobiles&mdash;especially his cherished MGBs. His work reflected a patient hand, an exacting eye, and a steady generosity in sharing his skills and stories with family and friends.
Win&rsquo;s warmth, quiet humor and dedication to his passions left a lasting impression on all who knew him. He will be remembered for his careful workmanship, his love of beauty in small things, and the steady presence he provided to his family.

Obituary for Maurice Irwin "Win" Gould, Jr. 

ObituaryMaurice Irwin “Win” Gould, Jr....

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Posting Activity

Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

JUN

3

4:30 PM

Highland Park, IL

Celebrate Highwood – Wednesday Evening Gourmet Market Music Lineup

JUN

3

6:00 PM

111 North Ave, Highwood, IL

The 79th Annual 57th Street Art Fair: June 6–7, 2026

JUN

6

11:00 AM

Hyde Park, IL

The 79th Annual 57th Street Art Fair: June 6–7, 2026

JUN

7

10:00 AM

Hyde Park, IL

Pride in the Park

JUN

17

4:30 PM

111 North Ave, Highwood, IL

Highland Park Announces 2026 EnjoyHP Lineup

JUN

19

5:00 PM

Highland Park, IL

Taste of Highland Park Returns June 19–20!

JUN

19

5:00 PM

Highland Park, IL

Highwood 5K Family Run, Walk & Stroll

JUL

18

9:00 AM

Highland Park, IL

ReHOME Estate Sale in Highland Park

Northbrook Garden Club Plant Sale Fri 5/15 (9-4) & Sat 5/16 (9-2)

Green Drinks - Come see nature photography! Speaker - Lisa Musgrave

Obituary for Maurice Irwin "Win" Gould, Jr.