Ashland to the Six Corners
Wicker Park takes its name from brothers Charles and Joel Wicker, who bought 80 acres along Milwaukee Avenue in 1870 and left behind the small park at its center. After the 1871 fire, well-off families built brick and stone mansions here, and Hoyne Street became known as Beer Baron Row. Artists followed the cheap rents in the 1980s, and the Around the Coyote arts festival started in 1989. Today N Milwaukee Ave runs southeast from the six corners in a long diagonal of record stores, bookshops and resale.
This route runs from the south end of the strip up to the six-corner crossing of Milwaukee, North and Damen, because the shops open in roughly that order. Dusty Groove opens at 9am, the record stores at 10, the resale shops at 11, and Quimby's and Myopic Books at noon. Myopic stays open until 8pm, so it makes the natural last stop. If you have records or clothes to sell, bring them: four shops on this route buy.
Start on Ashland: Dusty Groove
Dusty Groove (1120 N Ashland Ave) sits on Ashland at Haddon, one block south of Division and just off the strip. It sells new and used jazz, soul, funk, hip-hop, Brazilian and Latin LPs, CDs and 45s, with bins sorted into sections for Tropicalia, Afrobeat, reggae, vintage soul, French pop, blues and jazz. It opens at 9am every day. Everything in the shop is also listed on its website, so you can order ahead and collect at the pickup window, and stock that doesn't sell gets marked down quickly.
Selling works like this: Dusty Groove buys LPs, CDs and 7- and 12-inch singles from 9am to 5pm daily, and pays most for vintage, rare and obscure jazz, soul, hip-hop and funk, though clean rock records are welcome too. Email used@dustygroove.com or call 773-342-5800 with a description first. An appointment helps, walk-ins can face a wait, and you need a driver's license or state ID. For large collections it makes house calls around Chicago.
The South End: Shuga, Secret Agent and Reckless
Walk up to Milwaukee. Shuga Records (1272 N Milwaukee Ave) is a large, well-organized store with new and used vinyl across genres, plus cassettes, CDs, turntables, posters and zines. Time Out counts close to 20,000 records that are only for sale in the shop. Shuga is also a record label that has pressed Dehd and Ne-Hi, and its in-store stage, which came from Atomic Records in Milwaukee, has hosted signings and sets by Khruangbin, Faye Webster and King Gizzard & the Lizard Wizard. It is a regular Record Store Day stop, and a second Shuga is on Armitage in Logan Square.
A few doors up, Secret Agent Supply Co. (1276 N Milwaukee Ave) is the storefront for 826CHI, a nonprofit that runs free writing programs for Chicago kids. It sells spy-themed gadgets, children's books and literary gifts, and every purchase helps pay for the programs. It keeps short hours, Wednesday to Sunday from noon to 6pm, so time the walk around it.
Heading northwest, Reckless Records (1379 N Milwaukee Ave) is the Wicker Park branch of a Chicago chain that dates to 1988, with new and used vinyl, CDs and DVDs. Time Out says this shop has the chain's largest selection, and it sometimes hosts in-store performances and signings. Staff buy used music every day from opening until an hour before closing, so bring that box of records with you.
The Resale Row
Closer to the Damen Blue Line, the vintage and resale shops sit a few doors apart. Ragstock (1459 N Milwaukee Ave) keeps more than 10,000 vintage and used pieces with new arrivals daily, plus new basics and costumes, which makes it the useful stop in the weeks before Halloween. Buffalo Exchange (1478 N Milwaukee Ave) sells vintage, designer and everyday clothing, and Crossroads Trading (1519 N Milwaukee Ave) leans toward name-brand and designer resale.
Both Buffalo Exchange and Crossroads buy clothes for cash or trade. At Buffalo Exchange, sellers join a waitlist and need ID; Crossroads also takes overnight drop-offs. Right by Crossroads, Urban Outfitters (1521 N Milwaukee Ave) has a vinyl section if you still have room in your bag.
The Six Corners: Quimby's, Myopic and Barnes & Noble
Before you reach the intersection, detour east on North Avenue to Quimby's Bookstore (1854 W North Ave), at Wolcott, three blocks east of Damen. It stocks zines, small-press comics, graphic novels, underground literature and offbeat magazines. Time Out's August 2026 bookstore list singles out its range of new DIY and small-press zines and the zine club that meets around them. It opens daily from noon to 7pm. Look for it across from the bike shop with a bike hanging from a pole.
Back at the six corners, Barnes & Noble Wicker Park (1601 N Milwaukee Ave) fills the former Noel State Bank building, with toys, games and its own vinyl section. It hosts author signings, readings and children's storytimes, but posts no hours, so call ahead.
End at Myopic Books (1564 N Milwaukee Ave), which Time Out calls one of Chicago's oldest and largest used bookstores: more than 80,000 titles stacked floor to ceiling across three floors, with deep fiction, poetry and art sections. Staff will make recommendations, and the store keeps a no-phone policy, so plan to browse rather than call. It is open daily from noon to 8pm.
A Detour on Division
If you start or finish near Tortello, walk west on Division to Perpetual Books (2136 W Division St), which looks for unusual titles and pairs fiction and poetry with an archive of vintage magazines and used vinyl. It runs book clubs and pop-ups, and stays open until 8pm on Friday and Saturday.
Where to Eat
Mindy's Bakery (1623 N Milwaukee Ave) does takeout breads and pastries from the Mindy's Hot Chocolate team; get the mortadella and giardiniera turnover. On Damen, Dove's Luncheonette (1545 N Damen Ave) is a counter-seat Tex-Mex diner that suits a solo lunch, and Paulie Gee's (1566 N Damen Ave) sells New York-style pizza by the pie or the slice. Near the south end, Tortello (1746 W Division St) serves handmade pasta at the counter. For dinner after Myopic, Taxim (1558 N Milwaukee Ave) is upscale Greek, a few doors away.
Blue Line and Buses
The CTA Blue Line's Damen station sits right at the six corners, where this walk ends. To start at the south end, ride the #56 Milwaukee bus, which runs the length of the strip; the #72 North Avenue bus also stops near Quimby's. Metra riders can use Clybourn station (2001 N Ashland Ave), about a mile away. Street parking is metered.
Car-Free Sunday, Halloween and Black Friday
Sunday, Oct 25
The last Meet Me on Milwaukee of 2026 closes Milwaukee Ave to cars and buses between North/Damen and Ashland from 10am to 4pm, with live music, exercise classes, outdoor dining and sidewalk sales. It is a pilot series run by Alderman La Spata, the Wicker Park Bucktown Chamber of Commerce and the Chicago Department of Transportation, and it is free. Milwaukee becomes a tow zone from 12:01am and the #56 bus is rerouted, so take the Blue Line. It is also the last Sunday of the Wicker Park Farmers Market, 8am to 2pm at 1425 N Damen Ave.
Saturday, Oct 31
Halloween. Ragstock sells party and holiday costumes alongside its vintage racks, so make it a stop in the days before.
Friday, Nov 27
Record Store Day's Black Friday release day, with limited pressings that this year include a King Gizzard & the Lizard Wizard 3D zoetrope record and a 30th-anniversary Teenager of the Year from Frank Black. Shuga is a regular Record Store Day stop; call the shops to ask which titles they ordered and when the doors open.
