Those April umbrellas are tucked away, and May flowers are ready to show off! It’s a season filled with vibrant events, from Northbrook's Art in the Park to Evanston's Umbrella Arts Festival, plus plenty of ways to make Mother’s Day feel extra special. It’s the perfect time to get out and make the most of it.

Northbrook Art in the Park

Saturday, May 9 - Sunday, May 10

Village Green | 1810 Walters Ave., Northbrook


Art in the Park returns to downtown Northbrook’s Village Green Park on Mother’s Day weekend from 10am to 5pm each day! More than 80 artists will show and sell their beautiful creations, including paintings, sculpture, jewelry, ceramics, and more. Live music in the gazebo, festival food, and youth art activities make this a family-friendly event for all.

Mother's Day in Downtown Evanston

Celebrate and honor all the Moms with brunch, shopping, special gifts and activities!

Mother’s Day is Sunday, May 10


Make this Mother’s Day one she’ll always remember! Kick things off with a delicious brunch, then wow her with a gift that feels just right. From relaxing spa time to one-of-a-kind treasures at local shops - or even a fun day out with the whole family - Chicago’s North Shore has everything you need to make her feel truly celebrated.

Skokie Festival of Cultures, May 16–17!

Celebrate Skokie's tremendous diversity at the Skokie Festival of Cultures, Saturday & Sunday, May 16–17, 11am to 6pm at Oakton Park.

Learn to Make Waves this Summer!

Jump into sailing and windsurfing this summer with Northwestern University’s Sailing Center. 'Learn to' classes are great for beginners or anyone getting back on the water.

Evanston’s Mother’s Day House Walk

Sunday, May 10

Evanston History Center | 225 Greenwood St., Evanston


Step inside some of Evanston’s most stunning and historically significant homes, each with a story to tell. Tour beautifully preserved residences rarely open to the public, plus a new apartment building. Discover rich architectural and cultural heritage, including a stop at the Evanston Friends Meetinghouse – a memorable Mother’s Day of beauty, history and charm!

One Night Only Pop-Up Galleries all over Southeast Evanston

Browse locally made art and drink locally made craft beverages inside small businesses. A portion of proceeds benefits Evanston Made.

Umbrella Arts Festival

Saturday, May 30

Evanston Fountain Square | Corner of Davis St., Orrington Ave., and Sherman Ave., Evanston


The Umbrella Arts Festival is a celebration of Asian American art, music, dance, food and culture featuring over 65 artists, artisans and food vendors, traditional and contemporary performances, and hands-on art and cultural activities. The festival is free, and all ages are welcome to come and enjoy!

Kick off your summer with the Chicago Stars in Evanston!

The Chicago Stars are gearing up for the World Cup! On May 31, join the Stars for International Day. Enjoy family-friendly activities in the Fan Zone and cheer on soccer players from around the world!

North Shore Artisan Spring Market

Saturday, May 30 - Sunday, May 31

Downtown Winnetka Station | 754 Elm St., Winnetka


The North Shore Artisan Market celebrates the ingenuity of independently owned small businesses who channel their passions into creating one-of-a-kind products. Meet and shop with the artisans themselves and learn how they make their unique and functional creations. Shop small, local & sustainable! Please note this year’s new location.

Grapes on the Green

Enjoy an afternoon of wine tastings, light snacks, live music, art and games June 20 at Village Green Park in Northbrook.

Evanston Made opens store May 2

Expanding from online shopping to a new storefront at 822 Dempster Street, filled with original art, unique goods & events from local artists!

Victorian Garden Party

Sunday, May 31

Skokie Heritage Museum | 8031 Floral Ave., Skokie


Step back in time and party like it’s 1900 at the Victorian Garden Party! Enjoy croquet and other classic Victorian-era lawn games, light refreshments, and hands-on crafts and activities on the museum grounds. Join us for a charming, family-friendly afternoon celebrating 1900’s garden party traditions.

Pescadero Patio Is Open

Patio season is here on the North Shore. Walk in or reserve a table and enjoy it while you can.

The Angel Next Door

THROUGH MAY 10, 2026

Northlight Theatre, Skokie

Poor Behavior

THROUGH MAY 10, 2026

Oil Lamp Theater, Glenview

Argentina's Niños - Welcome to Argentina

THROUGH MAY 10, 2026

Kohl Children's Museum, Glenview

Max and Benny's The Comedy Nosh with Matt Drufke

MAY 1, 2026

Max & Benny's, Northbrook

Witchy Bitches 2nd Annual Macabre Spring Weekend

MAY 1-3, 2026

Palmhouse, Evanston

Love & Information

MAY 1-10, 2026

Wirtz Center for the Performing Arts, Northwestern University, Evanston

Evanston Rides

MAY 1, 2026 - OCTOBER 24, 2026

Various Locations, Evanston

Flea Market Frenzy

MAY 2, 2026

Oakton Community Center, Skokie

Central Street Spring's Alive

MAY 2, 2026

Central Street, Evanston

Family Fun Fest

MAY 2, 2026

Ignite Arcade, Skokie

Dog Man the Musical

MAY 2, 2026

North Shore Center for the Performing Arts, Skokie

Evanston Made's First Saturdays Evanston Art Events

MAY 2, 2026

Various Locations, Downtown Evanston

Cinco Brunch

MAY 2-3, 2026

Pinstripes, Northbrook

Central States Dahlia Society Show

MAY 2-3, 2026

Chicago Botanic Garden, Glencoe

Downtown Evanston Farmers Market

MAY 2, 2026 - NOVEMBER 7, 2026

University Pl. at Oak St., Downtown Evanston

Chicago Stars vs Portland Thorns FC

MAY 3, 2026

Northwestern Medicine Field at Martin Stadium, Evanston

Wilmette Historical Museum Open House

MAY 3, 2026

Wilmette Historical Museum, Wilmette

Touch A Truck Family Festival 2026

MAY 3, 2026

Northeastern Illinois Public Safety Training Academy, Glenview

Davina and the Vagabonds

MAY 3, 2026

Evanston SPACE, Evanston

Tommy Castro and the Painkillers

MAY 5, 2026

Evanston SPACE, Evanston

Jake Shimabukuro

MAY 5, 2026

North Shore Center for the Performing Arts, Skokie

Cinco de Drinko

MAY 5, 2026

Fat Rosie's Taco & Tequila Bar, Lincolnwood

MiniMakers Crafternoon

MAY 6-27, 2026

Wayfair, Wilmette

Wheeling Park District - Goat Yoga

MAY 7, 2026

Heritage Park Performance Pavillion, Wheeling

Marc Broussard with Sway Wild

MAY 8-9, 2026

Evanston SPACE, Evanston

David's Redhaired Death

MAY 8-10, 2026

Wirtz Center for the Performing Arts, Northwestern University, Evanston

Art, Theory, and Practice MFA Thesis Exhibition

MAY 8, 2026 - JUNE 14, 2026

Block Museum of Art, Northwestern University, Evanston

Sutton Lee Seymour - Super Ma'am - Saving the World is a Drag!

MAY 9, 2026

Community House, Winnetka

Northbrook Art in the Park

MAY 9-10, 2026

Village Green, Northbrook

Artemis presented by WDCB

MAY 10, 2026

Evanston SPACE, Evanston

51st Annual Mother’s Day House Walk

MAY 10, 2026

Evanston History Center, Evanston

Show & Tell: Work in Progress

MAY 12, 2026

Writers Theatre, Glencoe

Evanston Arts & Craft Beverage Crawl

MAY 14, 2026

Main-Dempster Mile, Evanston

Wayfair Sip & Shop X Soul & Smoke

MAY 14, 2026

Wayfair, Wilmette

Northbrook Park District - Freaky Friday: A New Musical

MAY 15, 2026

Northbrook Theatre, Northbrook

Skokie Festival of Cultures

MAY 16-17, 2026

Oakton Park, Skokie

Corky Siegel's Chamber Blues featuring Ernie Watts

MAY 17, 2026

Evanston SPACE, Evanston

Wilmette Annual Historic Housewalk

MAY 17, 2026

Wilmette Historical Museum, Wilmette

Sunday Jazz at the Square

MAY 17, 2026 - JULY 26, 2026

Fountain Square, Downtown Evanston

History of Old Orchard Walking Tour

MAY 20, 2026

Westfield Old Orchard, Skokie

Karaoke Night

MAY 22, 2026

Curt's Cafe, Evanston

Ladies Wine and Nine Golf Outing

MAY 22, 2026

Skokie Golf Course, Skokie

In The TIme of the Butterflies

MAY 22-31, 2026

Wirtz Center for the Performing Arts, Northwestern University, Evanston

Damn Yankees

MAY 22, 2026 - JULY 6, 2026

Theo Ubique Cabaret Theatre, Evanston

Chris Greene Quartet - CGQ Turns 21

MAY 24, 2026

Evanston SPACE, Evanston

Sam Bush

MAY 10, 2026

Evanston SPACE, Evanston

Wheeling Park District -Bark in the Park

MAY 30, 2026

Heritage Park Performance Pavillion, Wheeling

Umbrella Arts Festival

MAY 30, 2026

Fountain Square, Downtown Evanston

North Shore Artisan Spring Market

MAY 30-31, 2026

Downtown Winnetka Station, Winnetka

Chicago Stars vs San Diego Wave FC

MAY 31, 2026

Northwestern Medicine Field at Martin Stadium, Evanston

Everyone at Play

MAY 31, 2026

Kohl Children's Museum, Glenview

Victorian Garden Party

MAY 31, 2026

Skokie Heritage Museum, Skokie

Northbrook Symphony Orchestra: Romantic Essentials

MAY 31, 2026

Sheely Center for the Performing Arts, Northbrook

Skokie Farmers Market

MAY 31, 2026 - NOVEMBER 1, 2026

5127 Oakton St., Skokie

Job

THROUGH JUNE 14, 2026

Writers Theatre, Glencoe

Photography in Mali: Hamdia Traoré’s Marabouts of Jenne in Context

THROUGH JUNE 14, 2026

Block Museum of Art, Northwestern University, Evanston

Teresa Montoya: Tó Łisto (Yellow Water)

THROUGH JUNE 14, 2026

Block Museum of Art, Northwestern University, Evanston

Beneath the Surface: Labor and Consumerism

THROUGH JUNE 14, 2026

Block Museum of Art, Northwestern University, Evanston

Wilmette French Market

THROUGH OCTOBER 31, 2026

East of the Wilmette Metra Station, Wilmette

Centennial Farm Exhibit

THROUGH DECEMBER 31, 2026

Historic Wagner Farm, Glenview

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