Top 5 group activities for a guys’ weekend in Times Square
Gather your crew and take on New York City’s Times Square for an energetic weekend of fun, flavor, and camaraderie.
Edited by Kaitlyn Dreyling | November 13, 2025
Times Square buzzes with nonstop energy in the city that never sleeps, making it the perfect playground for a guys’ trip filled with adventure, laughter, and late-night memories. Whether you’re rallying friends for rooftop cocktails, catching a game, or diving into immersive group experiences, this guide spotlights the best things to do to maximize your time in the city’s most iconic neighborhood. With Times Square hotels steps from the action, planning is effortless, so you can focus on making every moment count.
1. Rooftop bars with skyline views
Kick off your weekend with a toast above the city lights at one of Times Square’s many rooftop bars. These elevated lounges feature panoramic views, creative cocktails, and a lively atmosphere that’s perfect for groups. Enjoy open-air seating, DJ sets, and signature drinks while soaking in Midtown’s electric energy — perfect for kicking off, winding down, or serving as the main event for your night out.
DoubleTree by Hilton New York Times Square South is steps from top nightlife venues, including the on-site Vue180 Rooftop, featuring views of the Empire State Building and heated igloos during the colder months. Enjoy spacious guest rooms with city views, a fitness center, and easy access to Times Square’s best bars.
2. Sports bars and barcades
Gather your crew and catch the game at one of Times Square’s bustling sports bars, where big screens, drink specials, and group seating set the stage for memorable nights. Whether you’re cheering for your team or just enjoying the environment, favorites like Beer Authority, Yard House, and Jimmy's Corner will fuel your group with energetic vibes and classic bar fare. For even more fun, bring your crew to an arcade bar like Coexist GameHouse, Dave & Buster's, or Lucky Strike Times Square. DoubleTree by Hilton Hotel New York Times Square West is ideally located in the heart of the action, making it easy to transition between daytime games and late-night adventures. Take advantage of the on-site restaurant and rooftop lounge, and, of course, don’t skip the signature warm chocolate chip cookies at check-in.
3. Comedy clubs and live entertainment
Laugh out loud at Times Square’s legendary comedy clubs and live music venues, where stand-up acts and improv shows promise a night of nonstop fun. Check out Comedy Village for laughs or The Iridium for live music. Many clubs offer reservations, group packages, and private seating, making them perfect for a guys’ night out. Hampton Inn by Hilton New York Times Square is an ideal home base, with easy access to the area’s top entertainment spots and late-night venues, plus a lobby bar, rooftop lounge, and free hot breakfast the next morning.
4. Escape rooms and adventure games
Challenge your crew with immersive escape rooms and adventure games, favorites for those looking for some friendly competition. Test your teamwork at The Escape Game NYC, at the SPYSCAPE interactive spy museum, and with Watson Adventures Times Square Grab 'n' Go Scavenger Hunt, among many others. After your wins, retreat to Homewood Suites by Hilton New York/Midtown Manhattan Times Square-South, NY to chill in your spacious accommodations, featuring Confirmed Connecting Rooms by Hilton™, fully equipped in-suite kitchens, streaming entertainment, and free hot breakfast.
5. Late-night snacks and social spots
Refuel and keep your action-packed nights going with late-night bites at Times Square’s bustling 24-hour diners, pizza joints, and casual bars. Whether you’re craving a classic New York slice or hearty comfort food, there’s something for every appetite. Many spots stay open well past midnight, making them ideal for post-adventure hangouts. Hilton Garden Inn New York Times Square North is near the area’s best food and drink options, plus features its own traditional Italian restaurant and a convenient 24-hour market.
Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.
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