Fun Cleveland/NEO Weekend Ideas: 9/8/23 – 9/10/23

September 8, 2023

Todd Hall

Cleveland/NEO This Weekend: Our Picks

Looking for some things to do this weekend in Cleveland and the surrounding Northeast Ohio area to make the most of your weekend? There’s so much to see and do, even for those who are already familiar with the area. Whether you’re a lifelong resident or a recent transplant, there’s always something new to discover in Cleveland and NEO. So why not get out and explore this weekend?

Cleveland Weekend Weather Forecast

Friday, September 8th

Dave Chappelle – Rocket Mortgage Fieldhouse

Dave Chappelle is set to embark on a new leg of his distinctive stand-up comedy tour, “Dave Chappelle Live,” with Live Nation as the tour’s producer. The tour will kick off with two special performances at Madison Square Garden in New York City and will continue with shows in various cities, including Cleveland, New Orleans, Chicago, and more. You can find the complete tour schedule below.

Dave Chappelle is widely regarded as one of the most exceptional comedians in history. In 2019, he was honored with the prestigious Mark Twain Prize for American Humor. Chappelle has received over 30 nominations and awards in television and film, showcasing his talent in projects such as his groundbreaking sketch comedy TV series, “Chappelle’s Show,” comedy specials, and memorable guest appearances on “Saturday Night Live.” His achievements include five Emmy awards, three of which were for his Netflix comedy specials, “Sticks & Stones” (2020) and “Equanimity & The Bird Revelation” (2018), and two for his hosting of “Saturday Night Live” in 2017 and 2021.

Walkabout Tremont – Tremont

Make sure to visit Kaiser Gallery during Friday’s Walkabout Tremont to experience what Collective Arts Network Journal has hailed as a “remarkable art exhibition.” The heart of the “Nowstalgia” showcase revolves around a yearning for a time that was more carefree, lighthearted, and innocent. Drop by Kaiser Gallery to enjoy a cocktail, wine, or beer, and witness firsthand how “Nowstalgia” is brimming with inquiries, suggestions, and reflections on life in both its physical and online manifestations in 2023.

Jay Pharoah – Pickwick and Frolic

Jay Pharoah is a highly-anticipated leading man in the entertainment industry. His upcoming films include Comedy Central’s “OUT OF OFFICE,” Catchlight Studios’ “THE BLACKENING” for Tim Story, the indie comedy “MORT IN SHERMAN OAKS,” and Timothy Scott Bogart’s take on the history of Casablanca Records, “SPINNING GOLD.” Over the past year, he has starred in Netflix’s “RESORT TO LOVE” alongside Cristina Milian and the Lionsgate thriller “PRIVATE PROPERTY.” In the previous year, he appeared in Universal’s “ALL MY LIFE” opposite Harry Shum Jr., Justin Simien’s critically acclaimed “BAD HAIR” for Hulu, and Lionsgate’s “2 MINUTES OF FAME” directed by Leslie Small. On television, he played “J.J. Evans” in ABC’s Emmy Award-winning Live in Front of a Studio Audience version of “ALL IN THE FAMILY” and “GOOD TIMES,” and currently hosts and produces Nickelodeon’s hit game show “UNFILTERED.” Pharoah is best known for his spot-on impressions, having spent six seasons as a cast member on NBC’s “SATURDAY NIGHT LIVE.” In 2017, he took on his first leading role as ‘Floyd Mooney’ in Showtime’s “WHITE FAMOUS,” executive-produced by Academy Award-winner Jamie Foxx.

Saturday, September 9th

Air Supply – MGM Northfield Park

The iconic soft-rock duo Air Supply is bringing “The Love In Love Experience” tour to Northeast Ohio with a stop at MGM Northfield Park – Center Stage on Saturday, September 9.

Waterloo Arts Fest – Collinwood

The Waterloo Arts Fest is an annual event that unfolds within the creatively thriving Waterloo Arts & Entertainment District, nestled in the lakeside community of Collinwood, Cleveland, OH. Throughout its two-decade journey, the festival has expanded its reach, yet its core essence remains firmly rooted in community spirit and a celebration of local artistry. Spanning seven hours each year, the Waterloo Arts Fest serves as a vivid reminder to both residents and guests of the abundant treasures within the Waterloo Arts District. It underscores the untapped potential waiting to be explored and celebrates the sheer delight of residing in a city neighborhood that thrives on its diverse and vibrant population.

Cleveland Ocktoberfest – Cuyahoga Fairgrounds

Cleveland’s Oktoberfest offers a wild array of festivities, from wiener dog races to beer stein-holding competitions, making it an unconventional yet enjoyable way to spend the extended weekend. Not to be overlooked, there will be an abundance of beer available, along with a delectable menu featuring knackwurst, bratwurst, wiener schnitzel, goulash, and pierogi.

Cleveland has evolved into a city known for its strong association with both beer and rock ‘n’ roll. Hence, it’s no surprise that the city hosts an outstanding Oktoberfest celebration. Each Labor Day weekend, the Cuyahoga County Fairgrounds transforms into a sprawling German Biergarten, complete with dirndls and beer steins shaped like boots to set the festive mood.

Sunday, September 10th

Cleveland Browns vs. Cincinnati Bengals – Browns Stadium

As the NFL season for 2023 kicks off, the Dawg Pound, Cleveland’s fervent and dedicated fan base, is eagerly anticipating the matchup between the Cincinnati Bengals and the Cleveland Browns. This intense rivalry never fails to deliver an exciting game, and this year promises to be no different. The Bengals, led by their dynamic young quarterback, are looking to make a statement early in the season and continue their ascent in the AFC North. On the other side of the field, the Browns are determined to defend their home turf and prove that they are serious contenders for the playoffs. As the two teams clash in Cleveland, the roar of the Dawg Pound and the thrill of the game will set the stage for what promises to be a memorable start to the NFL season.

Duran Duran – Blossom Music Center

The iconic New Wave rockers are making their triumphant return to the live stage with a tour that promises to transport fans to the golden era of industry-defining New Wave and dance-rock classics. This legendary band, boasting 2 Grammy Awards and a place in the Rock and Roll Hall of Fame, is set to kick off their “Future Past” tour this coming May. Make sure to mark your calendars for a special performance at the Blossom Music Center on Sunday, September 10, 2023. Joining them on this incredible journey will be special guests Nile Rodgers & CHIC and Bastille. Secure your tickets now and don’t miss the electrifying live comeback of ‘the wild boys’!

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