8 Tips to Make the Most of Madison’s Maxwell Street Days 2019

July 01, 2019

by Amanda Wegner, Amanda Wegner Communications

One of Madison’s most-anticipated summer events is just around the corner: Maxwell Street Days .

Slated for July 19-21 this year, this annual shopping event is not only a massive draw for State Street and adjoining streets, it’s the OG of Madison festivals.

“Maxwell Street Days is one of Madison’s original festivals that offers the opportunity to see store ‘personalities’ spill onto the street and connect with the community in a classic urban bazaar-type fashion,” says Amy Moore, owner of Little Luxuries , a specialty gift and accessory store located at 230 State Street.

Over the course of three days, about 60 businesses, including boutiques, specialty stores, restaurants and cafes, will have an outdoor presence on State Street and adjacent, offering shoppers the opportunity to take advantage of fantastic discounts offered by your favorite downtown businesses.

“If you’re looking for something fun to do outside on Madison’s most famous street, Maxwell Street Days is not to be missed! Enjoy seven blocks of outdoor shopping bargains and great food!” says Elizabeth Ganser of Fontana Sports , a specialty outdoor retailer located just off State Street at 216 N. Henry St.

Now in its 44th year, Maxwell Street Days offers bargains, culinary delights and music for more than 30,000 shoppers. Modeled after Chicago’s famed Maxwell Street outdoor market and urban bazaar that ran for more than 100 years between 1871 to 1994, the enterprising owners of Madison’s Martin’s, a long-gone clothing store and tailor shop in the 400 block of State Street, founded the outdoor sidewalk sale in 1975 to showcase the State Street shopping district, kickstarting Madison's very own Maxwell Street Days tradition.

While Maxwell Street Days is the city’s largest outdoor shopping event, it’s more than a summer sidewalk sale. It’s a community celebration, and celebration of the retailers that make Downtown Madison great.

“This event is an opportunity to celebrate the relationship between community members and local brick-and-mortar businesses on the most well-known street in the state of Wisconsin — State Street,” says Moore.

For Rob Bowhan, owner of August , a boutique at 414 State St. that offers rare streetwear and high-tier sneakers from major brands, this year’s Maxwell Street Days will be just his second go at it having opened in October 2017, but he loves how the event supports small business and brings people together.

“It supports small business. If you want cool boutiques and restaurants, you have to support brick-and-mortars, mom-and-pop shops,” says Bowhan. “We love to be here, engage with our customers, see all the new people come in.”

It’s also another way to connect IRL with others.

“Madison is so good about this stuff, offering family-friendly events like Kids in the Rotunda, Madison Night Market, farmers’ market, all that,” says Bowhan. “There is a tremendous amount of value in looking up from your phone, getting out and connecting. Maxwell Street Days is one way to do that.”

As an added bonus, check out members of the Madison Roller Derby squad, which will be cruising up and down State Street on skates to take care of garbage and recycling for the event.

If you’re planning to hit up Maxwell Street Days, our retailers offer their eight top tips for making the most of this signature downtown event:

  1. Arrive early for the best selection. The event kicks off on Friday, July 19 at 8 a.m. “If you get there early,” says Ganser, “you’ll experience less traffic and heat.”
  2. Most retailers will accept credit and debit cards, but having cash on hand is not only a good idea, it helps further support participating businesses by avoiding the charges associated with using plastic.
  3. Don’t forget your reusable shopping bags or your Radio Flyer Little Red Wagon, says Moore.
  4. It’s a rain-or-shine event, so be prepared for the weather; pack your umbrella and your sunscreen.
  5. Shop ahead: Bring your Christmas list to take care of your holiday shopping in advance, advises Moore.
  6. Come hungry. There are many different options for food and drink among the Greater State Street Business Association member businesses, including American, Greek, Indian, Japanese, Italian and more! Plus, there’s plenty outdoor seating for some epic people watching.
  7. Set aside some serious time to get the most of your Maxwell Street Days experience. “You need to hit all seven blocks, so you don’t miss any bargains or good food!” says Ganser. Adds Bowhan: “Make a day of it. Pop down to the Union, head up to the Capitol. Bring your friends and family along. Get lunch, pop into as many retailers as you can.”
  8. Be a repeat shopper: There is no shame in hitting up Maxwell Street Days on Friday. And Saturday. And Sunday. “You’ll get the most selection on Friday, but sweeter deals as the weekend progresses,” says Bowhan.

For more info on the 2019 Maxwell Street Days event inclduing a list of participating vendors, click here.

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