Fall city trips with the guys are usually built around the stadium: a Bears game on the lakefront in Chicago, the Lions at Ford Field, the Saints at the Superdome or Navy on a Saturday in Annapolis. That's not enough for me to want to pack the guys up and head out on a long weekend trip. Instead, I'm looking for the whole package and these ten cities lead that list, with the bars, steakhouses and walkable hotels that fill the hours around the game, followed by 11 more awesome football weekends built around legendary spots from Notre Dame in South Bend to the blue turf in Boise.
So as the weather gets colder and the days shorter, it's time to pick your favorite destination. Even though we chose to lead this piece with a photo of the Loews Arlington facing AT&T Stadium in the Dallas-Fortworth Metroplex area ... I'm going to start our list of top picks with one of my all-time favorite guys trip cities, Chicago, Illinois! A fall weekend in Chicago fits football, steakhouses, neighborhood bars, architecture and crisp lakefront weather into three days. From September through November the trees change along Millennium Park, the Chicago Riverwalk and the Lakefront Trail, and the architecture river cruises keep running until the boating season closes. Start with an architecture cruise on the Chicago River and drinks downtown before a steakhouse dinner. Build day two around a Bears home game, or explore the brewery scene and neighborhoods like the West Loop and Fulton Market before a night out. On day three, walk or bike the Lakefront Trail, then finish with deep-dish pizza and the Art Institute of Chicago, or head to Hyde Park for the Obama Presidential Center. Men's guide to Dubai bachelor parties: Ultimate luxury experiences from desert safaris to yacht charters. Experience skydiving and exotic car racing. Perfect for groups seeking premium adventures in this opulent destination. First-time cruiser connectivity made simple: ship Wi-Fi versus cellular day passes, which cruise lines include internet, security considerations for banking, and practical strategies to match your usage without overspending. Book your stay at Marriott Cancun, An All-Inclusive Resort. Enjoy comfortable accommodations & convenient amenities for business & leisure travelers. Villa Del Palmar Loreto is a great spot for a guys weekend or Mexican Mancation adventure in Baja. Promoted by FlowAds The fall calendar gives the city more reasons to pick a weekend. Chicago Gourmet usually lands in late September, and October brings Open House Chicago, the Chicago Marathon, the Chicago International Film Festival and neighborhood Oktoberfests. Line up the Bears schedule with those dates before booking. For a base, The Ritz-Carlton, Chicago overlooks the Magnificent Mile in the Gold Coast, with handmade pastas and premium steaks at Torali Italian-Steak, drinks on the Rooftop at Torali and live jazz on Wednesday nights. Arlo Chicago puts the group in the historic Atlantic Bank Building near Millennium Park, the Riverwalk and the Theatre District, with a weekday Lucky Hour at About Last Knife and Friday DJ nights. Our Chicago guide from a former local covers the rest of the city. Detroit can pack football, beer and a big dinner into one late-October weekend, with a Lions home game at Ford Field and the Detroit Fall Beer Festival at Eastern Market in the same stretch. The weekend below comes from Lisa's Chic Travel & Tours, a Detroit-focused travel advisor. Why we picked it: a grill you can actually carry to the campsite, the tailgate or the cabin without borrowing a truck. Stainless, no propane tank to wrestle, and hot enough to cook for four guys rather than reheat for one. Promoted by FlowAds Friday is Corktown: barbecue at Slows Bar BQ, then local beer at Batch Brewing Company. Saturday belongs to Eastern Market and the Detroit Fall Beer Festival, with Detroit City Distillery nearby and a polished dinner at Grey Ghost Detroit. Sunday is brunch, the downtown tailgate atmosphere and kickoff at Ford Field. Stay at the Detroit Foundation Hotel, in the city's former fire department headquarters, or the Shinola Hotel on Woodward Avenue, both downtown. Arlington, between Dallas and Fort Worth, puts AT&T Stadium and Globe Life Field within walking distance of its Entertainment District. Live! by Loews and Loews Arlington Hotel are connected by skybridge, share three pools, a spa and ten restaurants and lounges, and sit steps from the Cowboys' stadium. Start Friday with a drink at Bar Bourbon overlooking AT&T Stadium and USDA Prime steaks at Cut & Bourbon. On game day, tailgate on the hotel's Clover Club Lawn with views of the stadium, or watch on the property's big screens if the group does not have tickets. Between games, book behind-the-scenes stadium tours or a round at Texas Rangers Golf Club, and save Sunday morning for the pools or a treatment at The Spa at Loews Arlington. New Orleans in October gets cooler weather, Saints games at the Superdome and the run-up to Halloween in a city that leans into its ghosts, and the whole town is walkable without a car. Drop bags in the French Quarter and eat through it: a muffuletta at Central Grocery, dinner at Cochon, then live music on Frenchmen Street at the Spotted Cat, d.b.a. or Blue Nile. Gators & Ghosts runs airboat swamp tours into the bayou south of the city, with a 16-seat airboat or a private charter and pickup in the Quarter, plus nighttime ghost tours and a haunted pub crawl for a rowdier group. Late October usually brings the Krewe of Boo parade and an adults-only after-party. For a base, The Eliza Jane sits in restored 19th-century warehouses between the French Quarter and the Warehouse District, a short walk from the Superdome, with drinks in its library-style Press Room before a night out. Charlotte has deep NASCAR roots, with more than 90 percent of racing team shops in the region, and early October usually brings the fall race weekend at Charlotte Motor Speedway. Groups can take the NASCAR Race Car Experience behind the wheel or ride along, tour the garage area and Winner's Circle, and spend an afternoon at the NASCAR Hall of Fame with its Pit Crew Challenge and iRacing simulators. Off the track, the U.S. National Whitewater Center has a manmade Class III and IV whitewater river, and the Carolina Panthers play downtown. The Ballantyne handles the rest: Topgolf Swing Suites at Dunbar Social, dry-aged steaks finished over open flame at Gallery Restaurant, private-selection Maker's Mark and Woodford Reserve at Gallery Bar, and a four-bedroom Cottage for groups that want shared space. Annapolis gives a group a Mid-Atlantic weekend of Chesapeake Bay sailing, Navy football, steamed Maryland crabs and waterfront dining, all in a compact historic district that is easy to walk. Navy's October home games, including Homecoming, anchor the weekend. The Annapolis Waterfront Hotel is the only hotel directly on the harbor, with margaritas at Armada Dockside Cantina and prime steaks at Marmo Italian Chophouse. Take a private sailing trip on the bay, head to Navy-Marine Corps Memorial Stadium for the game, and tour the U.S. Naval Academy on the way out. Pasadena builds a guys weekend around UCLA home games at the Rose Bowl, with the USC rivalry game late in November as the loudest of the season. Friday is Old Pasadena, with a stop at Wild Parrot Brewing and dinner at Arroyo Chop House. Saturday is the tailgate and the game. On Sunday, take the Rose Bowl's behind-the-scenes tour through the 1922 locker room and the California High School Football Hall of Fame, then catch the day's games at a local bar. The Langham, where most visiting teams stay, brings old-school grandeur, while hotels in Old Pasadena keep the bars within walking distance. Bryan, the twin city to College Station, brings the Texas A&M gameday atmosphere without most of the campus crowds. The first night starts with barbecue at What's Tha Deal Barbecue, a drink at the Word of Mouth Speakeasy and a Texas two-step at Concrete Rodeo. On game day, eat tacos at Jesse's Taqueria, then watch at Gameday on Main or take the complimentary shuttle to Kyle Field, and finish at Hush & Whisper Distilling. Sunday is for Lake Bryan's trails, hats at Catalena Hatters and a Detroit-style pizza at Kinderhill Brewlab. Book The La Salle, a historic train-themed hotel with its own speakeasy, well ahead of home games. Boston combines a deep sports culture with harbor views and walkable nightlife. Mid-October has brought Patriots division games at Gillette Stadium, and the Celtics' fall schedule at TD Garden adds a second option. The Envoy Hotel in the Seaport has harbor and skyline views, fire pits on the Rooftop at The Envoy and Para Maria downstairs, led by two-time Chopped champion Tatiana Rosana, for lobster rolls and double smash burgers. Walk the Freedom Trail and Faneuil Hall on the last day for the history. Fall is Steelers season in Pittsburgh, a city of craft beer, riverfront neighborhoods and iconic architecture. Spend the first day exploring downtown and the riverfront before an afternoon of Pennsylvania craft beer, and give day two to the game on the North Shore. The Atterbury is a 300-room hotel in the historic Fulton Building, built in 1906 by architect Grosvenor Atterbury for Carnegie Steel's Henry Phipps. It sits steps from the Allegheny Riverfront and Market Square, and its Drafting Room restaurant pours Pennsylvania craft beer. Keep day three slow, with the city's museums and neighborhoods before a final dinner downtown. These 11 cities round out the fall football calendar, perfect for a fall guys trip and grouped by region. In Washington, DC, the Commanders play just east of the city in Landover, Maryland, and late September through October brings cool walking weather for the monuments, bars in Shaw and The Wharf, and soccer at Audi Field or hockey at Capital One Arena on the off day. In New York City, build a day around a Giants or Jets game at MetLife Stadium in New Jersey and save Sunday for Central Park, where the color runs from mid-October into early November, with Arlo Williamsburg as a base in Brooklyn's bar scene. In New Haven, tailgate for the Yale Bulldogs, take in fall color from the summit of East Rock Park and settle the pizza argument between Frank Pepe's and Sally's Apizza. Notre Dame Stadium anchors fall weekends in South Bend, and our college football stadium road trips cover the gameday details. In Ann Arbor, Michigan Stadium, the Big House, is the largest stadium in the country at a listed 107,601 seats, with a walkable college town around it. Nashville has Titans football, the Predators' season around the corner and more than 250 live music venues for the nights after the game. Knoxville fills Neyland Stadium for Tennessee Volunteers home games, and the Vol Navy tailgates by boat on the Tennessee River beside it. In Frisco, just north of Dallas, tour The Star, the Dallas Cowboys' world headquarters and practice facility, then play Fields Ranch East or West at Omni PGA Frisco. Denver has Broncos home games at Empower Field at Mile High and a deep craft beer scene, and The Curtis downtown has Hyper-Themed Rooms and a martini bar to start the night. San Francisco has some of its best weather in September and October, and the 49ers play south of the city at Levi's Stadium in Santa Clara, so pair the game with a bike ride across the Golden Gate Bridge. Boise State plays on the blue turf at Albertsons Stadium, and fall in Boise adds harvest season at the hop farms and Snake River Valley wineries west of town, plus hiking in the Boise foothills. Our fall guys weekend in Southwestern Idaho has the rest. A fall city weekend depends on how much of the trip the group wants to spend inside the stadium. NFL weekends in Chicago, Detroit, Arlington, New Orleans, Charlotte, Boston and Pittsburgh, plus DC, New York, Nashville, Denver and San Francisco, bring bigger stadiums and bigger cities. College weekends in Bryan, Annapolis, Pasadena, New Haven, South Bend, Ann Arbor, Knoxville and Boise swap that for tailgates and a gameday town, even in Pasadena's corner of Los Angeles. The strongest weekends on this list pair the game with something else: the Detroit Fall Beer Festival with a Lions game, or Open House Chicago and the Chicago International Film Festival with a Bears home date. Most of these cities have a slow Sunday option, from the Lakefront Trail in Chicago to the Rose Bowl tour in Pasadena, Lake Bryan's 20-plus miles of trails and the pools at the Loews hotels in Arlington. Book it for the morning of the flight home, before anyone checks out. 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Arlington, Texas - Cowboys Games From A Hotel Next Door
New Orleans, Louisiana - Saints Sundays, Swamp Airboats And Haunted Pubs
Charlotte, North Carolina - NASCAR Weekend And A Drive On The Superspeedway
Annapolis, Maryland - Navy Football, Sailing And Blue Crabs
Pasadena, California - UCLA At The Rose Bowl
Bryan, Texas - Aggie Gamedays Without The Campus Chaos
Boston, Massachusetts - Patriots, Celtics And The Seaport
Pittsburgh, Pennsylvania - Steelers Weekends And Pennsylvania Craft Beer
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