As we roll through downtown, we cruise past the dazzling lights of Playhouse Square, the largest performing arts district outside of New York City. Home to five historic theaters built in the 1920s, this vibrant stretch of Euclid Avenue has been beautifully restored and now hosts Broadway shows, concerts, comedy acts, and world-class performances year-round. Look up and you’ll see the iconic outdoor chandelier — the world’s largest outdoor chandelier — sparkling above the street. It’s one of Cleveland’s most Instagram-worthy spots and a symbol of the city’s cultural revival. This district is where old-school glamour meets modern energy, and it’s a perfect example of how Cleveland preserves its history while keeping things fresh and exciting.

As the trolley rolls into the center of downtown, we pass through Public Square, the historic heart of the city. Originally laid out in 1796 as part of Cleveland’s founding plan, this central gathering place has been the backdrop for parades, protests, celebrations, and everyday city life for over two centuries. At the center stands the Soldiers’ and Sailors’ Monument, honoring Civil War veterans, while the surrounding skyline showcases Cleveland’s architectural evolution — from early 20th-century landmarks to modern glass towers. Today, Public Square is a vibrant green space where locals gather for concerts, festivals, and winter ice skating. It’s where Cleveland’s past and present meet in one dynamic crossroads.

Guests will hop off the trolley for a short guided visit inside the historic The Arcade Cleveland, one of America’s first indoor shopping arcades, opened in 1890. Step beneath the stunning five-story glass skylight and admire the ornate ironwork, grand balconies, and intricate details that made The Arcade a symbol of Cleveland’s Gilded Age prosperity. Once home to luxury shops and social gatherings, this architectural gem has been beautifully restored and now houses shops, restaurants, and the Hyatt Regency Hotel. Your guide will share the story of its dramatic rise, near-demolition, and remarkable revival — a perfect example of Cleveland preserving its historic treasures while giving them new life.

Guests will step off the trolley for a short guided visit inside the historic Cleveland Public Library, one of the largest and most respected public library systems in the country. Inside the Main Library building, you’ll explore grand marble staircases, ornate architectural details, and beautifully preserved reading rooms that reflect Cleveland’s early 20th-century prosperity. Your guide will share how the library grew from a modest collection into a world-class research institution, serving millions of visitors each year. Guests will also see the peaceful outdoor reading garden tucked between the historic and modern buildings — a hidden gem in the heart of downtown — before returning to the trolley to continue the tour.

As the trolley makes its way along Cleveland’s scenic North Coast Harbor, riders pass three of the city’s most recognizable landmarks. First, you’ll see the striking glass pyramid of the Rock and Roll Hall of Fame, celebrating the legends and legacy of rock music from around the world. Designed by renowned architect I.M. Pei, this world-famous museum honors the artists who shaped the soundtrack of generations. Next door sits the hands-on, family favorite Great Lakes Science Center, featuring interactive exhibits, space exploration displays, and a NASA Glenn Visitor Center. Just beyond, along the Lake Erie shoreline, stands Cleveland Browns Stadium, home of the Cleveland Browns. On game days, this entire area transforms into a sea of orange and brown as fans gather along the waterfront. Together, these landmarks showcase Cleveland’s love of music, innovation, sports, and its beautiful lakefront setting.

As the trolley rolls into the historic Warehouse District, riders step back into Cleveland’s industrial heyday — with a modern twist. Built in the late 1800s, these massive brick buildings once stored goods arriving by rail and lake freight. Today, they’ve been beautifully restored into stylish loft apartments, award-winning restaurants, rooftop bars, and some of the city’s most energetic nightlife spots. You’ll notice the classic Romanesque architecture — thick brick walls, arched windows, iron details — all reminders of Cleveland’s booming manufacturing era. But instead of crates and cargo, you’ll now find patios buzzing with conversation and string lights glowing at night.

As the trolley curves along the river, riders pass through the vibrant Flats East Bank, one of Cleveland’s biggest comeback stories. Once the gritty heart of the city’s shipping industry, this stretch along the Cuyahoga River has transformed into a lively waterfront district filled with restaurants, music venues, riverfront patios, and skyline views. The boardwalk runs right along the water, giving visitors a front-row seat to boats cruising through the same river that powered Cleveland’s industrial rise. Today, the East Bank blends history and nightlife — historic bridges overhead, modern buildings lining the river, and the downtown skyline rising just beyond. It’s especially striking at sunset, when the water reflects the city lights.

Guests step off the trolley for a short guided visit inside the iconic West Side Market, Cleveland’s oldest continuously operating public market, open since 1912. From the outside, the market’s clock tower is one of the city’s most recognizable landmarks. Inside, the vaulted Guastavino-tiled ceiling stretches overhead while dozens of family-owned vendors line the aisles, selling fresh produce, meats, baked goods, cheeses, and international specialties that reflect Cleveland’s rich immigrant history. Your guide will share how the market became the heart of the surrounding Ohio City neighborhood and why generations of Clevelanders have made this their go-to spot for holiday shopping, Sunday ingredients, and favorite local treats. Guests will have a few minutes to explore, snap photos, and maybe grab a quick bite before returning to the trolley to continue the tour.

Guests hop off the trolley for a quick photo stop at the Cleveland Script Sign – Abbey Road, one of the city’s most popular skyline viewpoints. Perched in the Tremont neighborhood, this overlook offers a sweeping view of downtown Cleveland rising behind the bold red “Cleveland” script sign. From here, you can see the skyline stretch across the horizon, with the Cuyahoga River valley and historic bridges framing the scene below. It’s one of the best postcard-worthy views in the city — and the perfect place to capture a group photo, a family snapshot, or that must-share social media moment. Guests will have a few minutes to take photos before reboarding the trolley and continuing the tour.