48th Annual Monroe Street Festival

SATURDAY, SEPTEMBER 26, 2026

The Monroe Street Festival is a cherished annual tradition celebrating our many locally owned businesses and our surrounding residential neighborhoods. The purpose of the Festival is to promote and sustain new and existing businesses, enhance the positive and vibrant image of Monroe Street, and attract visitors from all over to our lively sliver of the city. The celebration, which is held annually on a Saturday in September, features a range of activities to bring the community together including local shopping, food and drink specials, outdoor entertainment, children’s activities, and so much more.

INTRODUCING THE Monroe Street Festival 2026 Trivia Hunt

Explore all of our street during the Monroe Street Festival, answering the questions on our new Trivia Hunt. Pick up a game sheet at Orange Tree Imports, Mystery to Me, Colectivo Coffee or Chocolate Shoppe Ice Cream. All the participating merchants have been asked to provide a silly or fun question about their business.

You will receive a list of about 30 questions. Just visit the business, find the answers, and fill it in on your challenge sheet.

Complete at least 6 of the questions, turn in your sheet at the Orange Tree Imports or Chocolate Shoppe Ice Cream, and you’ll be entered into a drawing for gift cards to one of our locally owned businesses!

Monroe Street Festival 2026

1700 Block

10:00-3:00 42nd annual Monroe Street Library League Book Sale, 1705 Monroe Street

10:00-5:00 Artsy Fartsy - Sidewalk sale; and special event featuring Dori Patrick, mixed media artist; Tinker And Spool - local artist; and Burda Growing Better - local garden coach and consultant.

10:00-5:00 Orange Tree Imports - Sidewalk sale & free silicone kitchen tongs to the first 400 customers making a purchase

10:00-5:00 Art Gecko - Sidewalk sale

11:00-1:00 Free Face Painting by Tiffany from Radiant Smiles at the corner by Basecamp Fitness - Sponsored by Landmark Credit Union

12:30 – 2:00 Monroe Street Art Center - Tween/Teen Maker's Market

Monroe Commons BY TRADER JOE’S

10:30 West A Cappella - Solos and duets by West High singers

11:00 Dave Landau – Interactive kid’s music

Noon Toco Beach Steelpan - Steel Drum Trio

1:00 The Currach Irish Quadtet - Celtic Music

2:00 Brass Knuckles - Brass & percussion quintet

3:00 Fixed Income – Rock and Roll from the 60’s and 70’s 

4:00 Mad City Funk – Classic Funk, R&B, Soul and Blue

1800 Block

10:00-5:00 D-Chai Thai Massage & Wellness. Massage Gift certificates 10 % off; Walk-in small tattoos with 30% going towards American Cancer Society research donation (1 or 2 inches square, $80 or $150, black and white only); Free eyebrow drawing and consultation.

10:00-5:00 MSN Plant Collective - Free plant tattoos for kids and 20% off all houseplants

10:00-5:00 Pizza Brutta - Outdoor Pizza Oven (in front of Barriques)

10:00-5:00 begonia. - Monroe Street Festival Grab & Go specials: Pulled Pork Burrito, Tacos, and Chips & Salsa

10:00-5:00 Bloom Bake Shop - Bloom Bus will be on Monroe Street selling seasonal pastries and sandwiches

10:00-5:00 Mystery to Me - Blind Date with a Book ($9.99); Golden Post-Its (find one in the store + win a prize!); Design-Your-Own-Bookmark Station; Raffle (one raffle entry with purchase of any amount).

10:00-5:00 Neuhauser Pharmacy - 15% off storewide (excludes prescriptions and USPS)

MONROE STREET at Harrison Street

10:00-5:00 Balloon Arch by Funny Faces Balloon Art

Celebrations Selfies Station sponsored by Orange Tree Imports

10:00-11:30 Free airbrush tattoos by Declan

Noon -3:00 U.W. Infant Learning Lab: sidewalk chalk activity and bubbles

1:30–2:30 Engine #4 from Madison Fire Department (if no fire emergency)

1900 Block

10:00 – Noon Alvarado Real Estate Group – Mini-carnival with games, free cotton candy, popcorn and prizes. Sponsored by Creando Exploratorium and Alvarado Real Estate Group

10:00-5:00 Monroe Street Framing - Take 10% off any custom framing orders placed during the Festival  (can't be combined with other discounts/offers).

10:00-5:00 Chocolate Shoppe Ice Cream food truck

10:00-5:00 Fya Syde Kitchen - The vibrant flavors of Jamaica, available in the restaurant or to go

10:00-5:00 Gallo Men’s Clothier - End-of-summer sale

10:00-5:00 Strictly Discs - 10 tables of bargains

10:00-5:00 Hive - Huge sidewalk sale

12:00 to 4:00 Clear Path Counseling & Wellness - Clear Path therapists will be handing out wellness products, playing games, and offering FREE 20-minute consultations with licensed mental health providers. (1934 Monroe Street)

10:00-5:00 Waltzing Matilda’s (coming soon to 1923 Monroe Street) - Look for the pink tent! Ellie and Annemarie will be there sharing more about the new restaurant, with treats and gift cards available for purchase.

10:00-5:00 Good Day Shop - Featuring an Ochabro Pop-Up with handcrafted matcha and specialty tea drinks.

10:00-5:00 Grapevine Massage and Bodywork - Free chair massage from 10am - 1pm, selling eye masks and hand-sewn accessories all day (business is located at 1914 Monroe St Ste 2 - will be set up across the street.

2500 Block

10:00-4:00 Collectivo - Pick-up the Monroe Street Festival trivia game

By CHOCOLATE SHOPPE ICE CREAM

10:00-Noon Free balloon art – Sponsored by Chocolate Shoppe

11:00-4:00 Bouncy Castle – Sponsored by Chocolate Shoppe

1:00-3:00 Free face painting – Sponsored by Chocolate Shoppe

11:00 Oak Apple Morris Dancers

11:45 Madison West Dance Team & the middle school Madison Royals

Noon Chicahuac Folklore Madison Mexican dance troup

1:00 Breckenridge Scottish Dancers

1:30 Trinity Irish Dancers

2:00 Eric de los Santos marimba

3:00 Mideast Salsa – North African Salsa Music

our 2026 MONROE STREET FESTIVAL sponsors