Roscoe Village was established in the early 1900s as a home for workers at the now lamentably defunct Riverview amusement park. These days, strollers have replaced roller coasters in this family-friendly North Side nabe packed with indie cafés and restaurants, such as Hero Coffee Bar, Paciugo, and Cuba 312. Roscoe Village continues to undergo dramatic changes—the unsightly overpass at Belmont and Western was demolished in March, a move to open up and bring life to the moribund western edge of the neighborhood. Also in the works: a two-lane bike trail above the Chicago River from Belmont to Montrose, scheduled to open in late 2017.
Where else can you check out a free-jazz or contemporary classical music show in a stunning minimalist setting? constellation-chicago.com
2. Hamlin Park
Lace ’em up for tennis, soccer, even boxing at this eight-acre green space. There’s also an outdoor pool (cannonball!). chicagoparkdistrict.com
3. Kerry Wood Cubs Field
You may catch the former Cubs pitcher at this new $5 million youth baseball park—he’s been known to hang out there. chicagoparkdistrict.com
4. Pencil Factory Lofts
The terra-cotta pencils on this building are a nod to its manufacturing roots. In 1937, it was also the site of Chicago’s first sit-down strike. 1800roscoelofts.com
5. WMS Boathouse
Marvel at the elegant Jeanne Gang–designed buildings before renting a kayak ($15 an hour) and gliding up the Chicago River. studiogang.com
6. Chicago Music Exchange
There’s a reason Rick Nielsen, Brad Paisley, Joe Bonamassa, and Adele (friggin’ Adele!) shop for top-of-the-line new, used, and vintage axes here. chicagomusicexchange.com
Get your fix of brightly colored tees and bold prints at this amiable boutique for moms and tweens. crushonroscoe.com
8. Father Time Antiques
You can drop a few bucks to get your watch repaired or spend $86,000 for a gorgeous historical timepiece at the Midwest’s largest seller of antique watches and clocks. (Psst: There are four rooms of furniture, too.) fathertimeantiques.com
Upgrade from Goodwill without breaking the bank at this popular spot, which blends salvaged and midcentury pieces with new. 2201 W. Belmont Ave.
Eat & Drink
Deep-dish naysayers might sing a different tune after they hit this classic spot (No. 9 on our 2015 list of Chicago’s best pizzas!), with familial roots that connect to Gino’s East. bartolispizza.com
Keep your fancy organic, gluten-free, shade-grown doughnuts. Old-school Dinkel’s has been around since 1922 and makes the most scrumptious chocolate cake–y treats around. dinkels.com
12. Scooter’s Frozen Custard
Best frozen custard in Chicago? Try telling us that’s not true after you’ve stuffed your face with a delish turtle sundae. scootersfrozencustard.com
13. Victory’s Banner
The servers all study meditation, which just might make this the chillest brunch spot in town. Bonus: When they sing “Happy Birthday,” they’ll tell you, “We love your soul’s rainbow-dream-promise-play!” victorysbanner.com
14. Village Tap
Why is this adored place always packed? The killer bar food. Or maybe the carefully curated brews. Wait, it’s gotta be the year-round beer garden. villagetap.com
May 7 The name says it all: Roscoe Village Neighbors hosts its annual Talk Derby to Me Spring Charity Pub Crawl.
May 13 Check out the experimental duo Whitehorse at Beat Kitchen.
May 14 Boutiques line the street with deals during the Roscoe Village Sidewalk Sale.
May 19 Broaden your electronic-music horizons with Son Lux at Constellation.
May 26 Hop on over to the Village Tap for its annual Art of Craft Beer event.
May 29 The improvisational jazz/psychedelia/ambient masters Carate Urio land at Hungry Brain.
Did You Know?
Jay Williams’s promising career as a Bull came to a crashing halt in 2003 when he smashed his motorcycle into a light pole at the corner of Fletcher and Honore.