Where to Go This September

  • Sonoma County
  • Telluride, Colorado
  • Orlando, Florida
  • Eastern Shore, Maryland
  • Chicago, Illinois
  • New York City, NY
  • Lisbon, Portugal
  • Singapore
  • Jerusalem, Israel
  • Sedona, Arizona

    Sedona, Arizona

    Temperatures in the high deserts of the American Southwest begin to drop in September, making it a wonderful time to get out and enjoy the great outdoors. It's also an event-filled month in Sedona; the month kicks off with the annual Red Rocks Music Festival, featuring classical and jazz musicians, and wraps up with Sedona Winefest, a two-day celebration of Arizona's rapidly expanding wine industry.

    Photo courtesy of Comstock Images/Thinkstock

  • Sonoma County

    Sonoma County

    There's no better time to visit Sonoma than during the annual grape harvest, when you can see the wine-making process in full swing. September represents a sweet spot, as vineyards are already harvesting grapes but the major harvest season events – and the inevitable crowds – don't occur until October. That means prices aren't so high and you won't have to fight for elbow space in the tasting room.

    Photo courtesy of Jupiterimages/Thinkstock

  • Crowds at the annual Telluride Blues & Brews Festival

    Telluride, Colorado

    Leaf peeping, film screenings, beers and blues ... these are just a few reasons why you should make your way to the mountains of Telluride this September. Besides being a beautiful time of year weather wise, this month also sees two of the city's signature events come to town, the Telluride Film Festival over Labor Day Weekend and the Blues & Brews Festival mid-month.

    Photo courtesy of Barry Brecheisen - Blues & Brews Festival

  • Getting ready for the parade in Disney World

    Orlando, Florida

    The kids are back in school, and that means you'll spend less time waiting in lines and more time enjoying the rides and attractions of Orlando's numerous amusement and water parks. If you don't mind getting rained on in the afternoons, you'll find hotel prices to be at their lowest during this low-season month. Foodies will love Orlando in September, as the city's restaurants come together for Magical Dining Month.

    Photo courtesy of Loren Javier

  • The historic Drum Point Lighthouse on Chesapeake Bay

    Eastern Shore, Maryland

    For the perfect fall road trip, head to Maryland's Eastern Shore, hugging the Eastern side of the Chesapeake Bay. The marshy flatlands are dotted with quaint New England fishing villages – great places to pull over for a no-frills meal of Maryland crabs coated in Old Bay. With its proximity to Washington, DC, this swath of rural Maryland makes a wonderful weekend getaway from the big city as well.

    Photo courtesy of Mr. T in DC

  • Millennium Park

    Chicago, Illinois

    Sports fans will love Chicago in September, as both Major League Baseball teams wind down their seasons and the Chicago Bears are just getting started. September also brings beautiful weather and the World Music Festival to the city, giving autumn travelers even more reasons to choose the Windy City.

    Photo courtesy of ©Cesar Russ Photography

  • Empire State Building at Sunset

    New York City, NY

    Autumn in New York ... there's a reason this city during this season earned a movie title. It's beautiful. Temperatures hover in the 60s and 70s, the New York Film Festival comes to town and its possible to snag discounted hotel rates. Sports fans can cheer the Yankees and Mets into the post season, while fashionistas descend upon the Big Apple for Mercedes-Benz Fashion Week.

    Photo courtesy of Ralph Hockens

  • Lisbon at sunset

    Lisbon, Portugal

    During Lisbon's fall shoulder season, prices and temperatures drop while crowds disperse, making September one of the best months to plan a visit. Temperatures are still warm enough to enjoy a wander through its switchback streets yet cool enough to duck into a cozy bar for a glass of port and nostalgic, mournful fado. As the European soccer leagues get started for the new season, be sure to catch a game if you can.

    Photo courtesy of Francisco Antunes

  • Singapore


    Weather-wise, there isn't really a bad time to visit Singapore, thanks to its position just north of the equator. It's hot throughout the year, but September tends to be dry. Perhaps the biggest reason visitors come to Singapore in September is to see the Formula 1 Singapore Grand Prix, the first night race on the F1 circuit. Even if you don't like racing, the event brings with it a huge party and ample live entertainment.

    Photo courtesy of

  • The Wailing Wall in Jerusalem

    Jerusalem, Israel

    Any student of religious history probably has the city of Jerusalem near the top of their bucket list. This city at the heart of three major religious faiths is a study in contrast – a place where ancient ruins sit alongside trendy, modern coffee shops. September is an interesting time to visit as Rosh Hashana, the first of the High Holy Days occurs early in the month.

    Photo courtesy of bachmont


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