Cleveland is the underdog city on Lake Erie that gave the world the Rock and Roll Hall of Fame, a world-class art museum (free on Sundays), the best food market in the Midwest (West Side Market), and LeBron James. It’s a post-industrial city in genuine cultural renaissance, with a thriving arts and restaurant scene in neighborhoods like Ohio City and Tremont.

Cleveland: The Underdog City That Keeps Winning Me Over

Every time I visit Cleveland, I leave thinking the same thing: why doesn’t everyone know about this place? It’s a city that’s been the butt of jokes for decades — the burning river, the sports heartbreaks, the rust belt decline — and yet Cleveland in the 2020s is a genuinely fantastic place to spend a long weekend. The museums are world-class. The food scene is thriving. And there’s a scrappy, self-aware pride here that makes the whole city feel like it’s rooting for you.

The Rock Hall: More Than a Tourist Trap

I’ll admit I walked into the Rock and Roll Hall of Fame expecting a glorified Hard Rock Cafe. I was wrong. I.M. Pei’s glass pyramid on the Lake Erie waterfront houses a thoughtful, sprawling celebration of rock music’s history — from the Delta blues roots through punk, hip-hop, and everything in between. The interactive exhibits are genuinely engaging, and the temporary exhibitions rotate enough that repeat visits feel fresh. I spent four hours and could have stayed longer. Tickets are $30 for adults. Pro tip: go on a weekday morning when school groups haven’t arrived yet, and you’ll have entire floors to yourself.

The rooftop terrace has one of the best views in the city — Lake Erie stretching out to the horizon on one side, the downtown skyline on the other. On a summer evening, it’s pure magic.

Cleveland Museum of Art: The Best Free Museum You’ve Never Heard Of

This is the hill I will absolutely die on: the Cleveland Museum of Art is one of the finest art museums in America, and it’s completely, always, no-exceptions free. The collection spans 6,000 years and includes works by Caravaggio, Monet, Picasso, Warhol, and an outstanding collection of Asian art that rivals the Met’s. The Ames Gallery of Medieval Art feels like stepping into a cathedral. The museum’s ARTLENS Gallery uses interactive technology to let you explore the collection in ways I haven’t seen anywhere else.

I’ve visited three times now, and each time I discover entire wings I somehow missed. Budget at least three hours, and don’t skip the outdoor sculpture garden.

West Side Market: Cleveland’s Beating Heart

West Side Market has been operating since 1912, and walking through its vaulted, terracotta-roofed hall feels like stepping into a European market you’d find in Barcelona or Budapest. Over 100 vendors sell everything from Hungarian sausages and fresh pasta to Middle Eastern spices and Slovenian potica. This is Cleveland’s immigrant heritage on full, delicious display.

My routine: start with a bratwurst and sauerkraut from Frank’s Bratwurst ($6-8), wander the produce arcade, grab baklava from the Mediterranean stall, and leave with a bag of pierogi from one of the Polish vendors. Saturday mornings are the busiest and most electric — get there by 9 AM to beat the crowds. The market is closed Tuesdays and Thursdays.

Ohio City, the neighborhood surrounding the market, has exploded with breweries and restaurants. Great Lakes Brewing Company ($6-8 pints, $13-20 entrees) is the anchor — their Christmas Ale is legendary, but the Edmund Fitzgerald Porter is the one I order year-round. Market Garden Brewery across the street is equally excellent.

Tremont: The Neighborhood That Stole My Heart

South of downtown, Tremont is a compact, walkable neighborhood of Victorian homes, art galleries, independent restaurants, and one of the best neighborhood vibes in the Midwest. Every second Friday of the month, the Tremont Art Walk opens galleries and studios to the public — it’s free, and the energy is wonderful.

For food, Dante ($22-38 entrees) serves outstanding Italian-inspired dishes in an intimate setting — the pasta is handmade, and the wine list leans toward interesting Italian and Spanish bottles. Parallax ($20-35 entrees) does creative Asian-meets-Mediterranean fusion that sounds gimmicky on paper but works beautifully on the plate. For something more casual, Prosperity Social Club ($11-18) is a 1930s-era bar serving elevated comfort food — their pierogies and chicken paprikash are the real deal.

Lucky’s Cafe ($10-16) does one of the best brunches in Cleveland — inventive dishes using local, seasonal ingredients in a cozy, no-frills space. Expect a weekend wait, but it moves fast.

Playhouse Square and Downtown

Playhouse Square is the largest performing arts center in the country outside Lincoln Center, and the restored theaters are absolutely gorgeous. Even if you don’t catch a show, walk through the lobbies of the State, Palace, and Ohio theaters — the GE Chandelier hanging over Euclid Avenue at the center of the district is the world’s largest outdoor chandelier and makes for a great photo.

Downtown Cleveland is compact and walkable. The Arcade, a five-story Victorian shopping arcade built in 1890, is architecturally stunning — it’s now a Hyatt hotel, but you can walk through the atrium freely. East 4th Street is a pedestrian-friendly block of restaurants and bars that gets lively on weekend nights. Try Greenhouse Tavern ($16-28 entrees) for creative New American cooking, or Lola Bistro ($22-40), Michael Symon’s flagship restaurant that put Cleveland’s food scene on the national map.

The Waterfront and Beyond

Edgewater Park, on the west side of the lakefront, has a beautiful beach and some of the best sunset views I’ve seen anywhere. Pack a picnic, bring a six-pack of Great Lakes Brewing, and watch the sun drop into Lake Erie. It costs nothing, and it’s unforgettable.

For a day trip, Cuyahoga Valley National Park is just 30 minutes south — the Brandywine Falls trail is an easy, gorgeous hike, and the Cuyahoga Valley Scenic Railroad runs through the park if you want to take in the views from a vintage train car. Cedar Point, the roller coaster capital of the world, is about an hour west on I-90 — pair it with a night in Sandusky for a proper amusement park pilgrimage.

Where to Sleep

Budget: The HI Cleveland Hostel (from $32/night dorm bed) in Ohio City is well-run and walking distance to West Side Market and Great Lakes Brewing.

Mid-Range: The Kimpton Schofield Hotel ($160-220/night) downtown occupies a gorgeous 1902 building with stylish rooms and a solid lobby bar. The Metropolitan at the 9 ($170-240/night) in the old Cleveland Trust Building has a jaw-dropping atrium.

Luxury: The Ritz-Carlton Cleveland ($300-450/night) delivers exactly what you’d expect, with lake views and a prime downtown location. For something more unique, try Glidden House ($220-350/night) in University Circle — a 1910 mansion turned boutique hotel steps from the art museum.