Posted on
September 30, 2025
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Trip Ideas
When he concluded one of history’s most famous trips six centuries ago, little did Christopher Columbus know his October arrival in the New World was perfectly timed; today the weekend that commemorates his trip is an ideal post-summer, pre-holiday excuse for a fall getaway.
IgoUgo members who have taken advantage of the long weekend to travel say these six places peak come Columbus Day (October 12 this year).
New York City
Perhaps no city loves a parade more than New York, and Manhattan’s Columbus Day procession has grown to become the world’s largest celebration of Italian-American heritage. First held in 1929, it is today a two-day event featuring a wreath-laying ceremony at Columbus Circle, the parade, and a mass at St. Patrick’s Cathedral. New Yorker Ishtar promises it's a party not to be missed.
Hancock, MA
Elusiveck says that Columbus Day in this Berkshire town is “even better than winter,” with “lots more to do.” Attractions include the Mohawk Trail, Mount Greylock, fall festivals (she attended a powwow), and the flower bridge of nearby Shelburne Falls. CJohnsto enjoyed simple pleasures like seeing “houses decorated for fall, pumpkins, cornstalks, and scarecrows,” sometimes looking quite lifelike--or at least like a realist painting.
Lone Pine, CA
October 9-11 marks the Lone Pine Film Festival, a celebration of Western-genre filmmaking that Bruce says is “a lot of fun.” And he gives us more reasons to go: “The real charm of this festival is its setting, the Alabama Hills with Mount Whitney as a backdrop. Given the setting and the festival, this trip can make a perfect weekend getaway while allowing the visitor to relax in the splendor of the Eastern Sierra.”
Chincoteague Island, VA
“Over Columbus Day weekend, the island becomes almost as crowded as it is during the week of the annual pony swim, as seafood lovers come from all directions for the annual Chincoteague Oyster Festival,” says Webgoddess. The island (pictured above) boasts local bands, games, a cooking contest, and plenty of food options, but Webgoddess sticks to slurping: “As an oyster lover (and these are the best on the East Coast), I usually skip the side dishes and feast strictly on oysters.”
Jackson, NH
A classic White Mountain town most of the year, Jackson stands out during the first few weeks of October with its returning Pumpkin People. Gail&Jim describe the gourd invasion as “local merchants and citizens decorating pumpkins in creative ways (some of them building tableaus of Pumpkin People families).” That just might be an understatement; check out this sneak preview, sure to crack you up.
Buenos Aires, Argentina
In Argentina, Columbus Day gets a new season--spring--and a new name, Día de la Raza. It also gets a new focus as a salute to Latin American culture. It’s still an official holiday, though, so a three-day weekend is observed and public celebrations are held. On Sunday, don’t miss the Feria de Mataderos, a weekly spring event that offers a bit of Argentine cattle country in the city. First-time BA visitor viajera67 attended and enjoyed watching dancing and riding competitions while feasting on “delicious beef and beer.”