Find a Trail that feels like you. Save the good spots, explore at your own pace, and make a few memories along the way.
Start with the public library, browse the Southside streets with an optional Butler coffee, and end at Naked Tomato’s newly opened Kent Avenue dining room. Make a dinner reservation and check the library’s daily hours.
Explore these counters and dining rooms over several visits. Polish breads and pierogi sit alongside a neighborhood deli and Lebanese pantry; give each cuisine its own meal.
Food and drink addresses to return to on separate visits: pantry shopping, handmade tortillas, pizza, Iranian cooking, cake and chocolate. Pick one main meal per trip; restaurant reservations and factory-shop hours vary.
A collection for separate visits, from Italian pantry shopping and coffee to a sit-down dinner, a brewery visit or a sundae. Choose a daytime sandwich-and-bakery trip or book one evening restaurant, leaving the other stops for another day.
Choose a different breakfast or casual lunch on separate visits. Compare neighborhood bakeries, Taiwanese pastries and slice counters; a kiosk is included for a quick takeaway rather than a sit-down meal.
Indoor market stops for many lunches. Choose one meal or snack, browse a pantry shelf and explore the rest on separate visits. Individual vendors set their own hours.
Counters and shops for separate visits. Choose one main dish and perhaps one takeaway treat each time. Vendor schedules differ from the market building’s hours.
Independent food-shopping stops to explore over several visits. Choose a few ingredients for a meal at home, carry a cool bag for perishables and keep prepared food purchases small if you also plan lunch.
A collection of bakeries, dessert counters and cafe breaks for separate visits. Pick two or three stops, share what you buy and return for another comparison instead of attempting every sweet in one day.
A collection for separate visits around Vanderbilt and Washington avenues: bakery mornings, neighborhood dinners, Korean tacos and ice-cream stops. Pick a restaurant for one visit and pair it with dessert, leaving the other tables for another day.
Choose Melba’s as the main meal, walk to a public park and finish with one scoop. Start early enough for daylight in the park and check restaurant seating before you go.
Pair an afternoon around the Museum of the Moving Image with book browsing and dinner at Kam Rai. Recent local coverage makes this a good moment to revisit the Thai restaurant; book a screening separately if one fits.