Saturday

5. Hitting the Trail, 9 a.m.

Grab a well-made cappuccino at Caffé Streets and head for the Wood Street entrance to the 606, once an elevated rail line, now a wide, welcoming walkway that takes runners, strollers and cyclists through northwest-side neighborhoods. Urban and pastoral meet-up: The El rolling overhead at Milwaukee Avenue. On North Humboldt Boulevard you’ll find the marker at 1667, where L. Frank Baum wrote “The Wonderful Wizard of Oz” (his home has since been torn down). Follow your own mellow, quick road to North Avenue and Roeser’s Bakery, in business since 1911. Allow time for scouting before taking a number — Swedish flop coffee cakes, maple bacon long johns and a boatload of bismarcks (pastries from $1.19). Take them across the street to Humboldt Park, where the statue of the explorer Leif Eriksonspeaks (it’s part of the Statue Stories Chicago program). This Leif, the voice of the Second City alum Fred Willard, gives props to himself and gently disses Columbus (Columbus could not be reached for comment).

6. Art in the Park, 11 a.m.

The National Museum of Puerto Rican Arts & Culture (free) is in the oldest surviving structure in Humboldt Park: stables built in the 1890s. Inside the red-roofed building with its gables and turrets, contemporary Puerto Rican art is on view (paintings by Oscar Luis Martinez, who lives in the city, were recently shown in the second-floor gallery).

7. A Jibarito and Cabrito, 1 p.m.

You can go the buffet route or get table service at La Palma, a cheerful Puerto Rican cafe in Humboldt Park (in a mural, a grinning frog plays the bongos). Take the table; that way you can ask the enthusiastic servers which filling they recommend in the jibarito ($7.75), the sandwich in which disks of plantain serve as a crisp bun; you can’t go wrong with pernil(slow-roasted pork). The tender cabrito (goat stew), a weekend special, is another must ($12.95 with side dishes).

8. Ice Cream Dreams, 2 p.m.

Claim a stool at Spinning J, a sweet twirl on an old-time soda fountain (the 1920s marble counter came from a pharmacy in Milwaukee) opened last year by the baker Dinah Grossman and Parker Whiteway. Ms. Grossman makes outstanding pies — banana cream drizzled with caramel, lemon Shaker (from $5) — and shakes, sodas and floats (from $6.50) are superb. The sassafras in the house-made root beer: foraged.

9. Get to the Greek, 7 p.m.

The chef David Schneider was of the opinion that Greek cuisine, and culture, had become something of a “cartoon” and he didn’t like it. So he devised his excellent restaurant Taximin Wicker Park to “show that there’s regionalism in Greece.” Try the fried cauliflower with whipped feta ($8); the cloud of tzatziki with cucumbers and dill ($6); the duck gyro with a pomegranate reduction ($25); and a bottle of Greek red from a list deep with discoveries. Mr. Schneider, whose mother is Greek and who has spent considerable time there, makes his own yogurt and breads (the pita is outstanding). It’s a good-looking place — vaulted ceilings, copper-topped tables — with an abundance of energy. The rooftop recently opened for the season. At this elevation, Mr. Schneider will be serving lamb roasted as shepherds doin the mountains of Crete.

10. Blues Project, 9 p.m.

The Happy New Year banner was still up in April at Rosa’s Lounge in Logan Square, but it doesn’t seem out of date — this is an upbeat place, from the greeting at the door to the dynamic performance by Lil’ Ed & the Blues Imperials (weekend tickets $12 to $20), led by Ed Williams, who plays a scorching slide guitar. Rosa Mangiullo and her son Tony, a drummer, opened the club 32 years ago, after moving to Chicago from Milan. “To me blues is an honest form of expression,” Mr. Mangiullo said. Vaclav Havel, then the president of the Czech Republic, was in the house in 1993. Magic Slim played — Mr. Havel’s request.

11. Tiki Time, 11:30 p.m.

The cocktail magazine Imbibe named Lost Lake its bar of the year for 2016, and three sips into a Tic-Tac-Taxi (two rums, coconut, passionfruit, lime; $12), you are pretty sure the vote was unanimous. This blast of “Blue Hawaii” comes from Paul McGee, among the city’s most praised bartenders, and Shelby Allison, his wife. Drinks are beautifully balanced; the Lost Lake with aged rum and pineapple has a nip of Campari ($12), and sherry sidles into more than one cocktail. The room nods to places like Don the Beachcomber — lots of bamboo, banana-leaf wallpaper — and the soundtrack includes new-wave surf (“Bikini Sunset” by the Volcanos) and reggae. It’s a giddy getaway; the banana adorning a daiquiri, carved to resemble a dolphin (complete with clove eyes), really is smiling at you.