Top 10 Columbus Day Weekend Getaways

Compared to Memorial and Labor Day, Columbus Day often seems like the unsung hero of all the three-day weekends. Yet it's Columbus Day's lack of holiday traditions that make it the perfect time to travel. Instead of feeling obligated to go to an annual Memorial or Labor Day picnic, you're free to make whatever travel plans you wish. Plus, you'll miss the summer crowds that accompany Labor and Memorial Day vacations - and better still, you can often find cheaper rates at area vacation rentals, since October falls in the off-season of many areas.

Ready to start planning your Columbus Day trip? Here are the top 10 Columbus Day weekend getaways.

columbus day paradeNew York City

From the fall foliage in Central Park to Halloween events all over the city, October is a wonderful time to visit the Big Apple. The most obvious reason NYC wins the top spot on this list of Columbus Day weekend getaways is the city's massive Columbus Day parade , but the Boo at the Zoo , Haunted Pumpkin Garden , and family-friendly events at the Met are other worthy attractions.

San Francisco

As the oldest Italian-American celebration in the country, the San Francisco Columbus Day Celebration and Italian Heritage Parade is over 140 years old. After the parade, spend the day sampling Italian delicacies in San Francisco's North Beach neighborhood .


There's never a quiet weekend in Beantown - and Columbus Day is no exception. You're guaranteed to stumble upon several holiday-themed events, from killer Columbus Day sales on posh Newbury Street to the Tufts Health Plan 10k in Boston Commons to the North End's Columbus Day Parade .

Montauk, New York

Though the beautiful scenery of Montauk is worth the trip alone, the Montauk Chamber of Commerce Annual Fall Festival also takes place on the three-day weekend. Don't miss a chance to sample the area's best clam chowders at the Famous Clam Chowder Tasting Contest .

miami columbus day regattaMiami

A far cry from the other foliage-filled Columbus Day weekend getaways on this list, Miami hosts the Columbus Day Regatta , where party lovers from around the world grab any seafaring vessel they can find and sail to Key West. What results is a nonstop three-day party that puts Mardi Gras to shame. If you're more interested in drinking and dancing than hiking and history, this is the destination for you.


Denver's Italian-American community throws one of the largest Columbus Day parades in the country. The fun doesn't stop after the last marching band crosses the finish line, however; there's also a post-parade celebration with plenty of Italian food and drink.

Newport and Providence

Easily split your time between two of Rhode Island's best cities. Raise a glass (or stein) at Newport's International Oktoberfest or ogle pumpkin-carved art at Providence's Jack-o-Lantern Spectacular . Best of all? It's only a 45-minute drive between the two cities.

Burlington, Vermont

Few Columbus Day weekend getaways are more bizarre than Burlington, Vermont. The town is home to the annual Giant Pumpkin Regatta and Festival , where participants race giant hollowed-out pumpkins on Lake Champlain.

The Poconos

Escape to the rugged Pennsylvania mountains on Columbus Day to enjoy perfect weather for autumn hiking, apple picking, and pumpkin carving. The area's sweeping expanses of fall foliage will surely put you in the fall mood. Be sure to bring your camera!

Lake Placid

As if the natural beauty Lake Placid wasn't enough to entice you, the area also hosts the Flaming Leaves Festival , home of ski jumping competitions, horseshoe tournaments, dye-your-own tie dye, and plenty of live blues music.


Book an NYC Rental

One-Bedroom Suite in Private Manhattan Townhouse, maximum three guests

Large private bedroom suite in a historic Manhattan Townhouse, ten minute subway ride to Time Square. Treat yourself to spacious, quiet, luxurious b&b style accommodations at a reasonable cost. We invite you to make yourself at home in this histo...

Luxury Condo Minutes from 5th Avenue

Welcome to The Jade. Enjoy ultra hip luxury in this new building designed by Jade Jagger and Philippe Starke, the attention to details never disappoints! From the sub zero refrigerator, to the state of the art Penthouse club. Many of our guests f...


We are conveniently located in one of the most desirable areas in NYC: 2 blocks from 'Fairway Market' six blocks from 'Lincoln Center' 3 blocks to gorgeous Central Park and popular 'Trader Joes Market' is just steps away. Our bright designer fur...

Elegant NYC Pad with wifi

Downtown, elegant New York City apartment! High ceilings, newly renovated and tastefully designed. There is room for 12! The Rate of $150 per night applies for two people. After that it is $40 per person per night. Walk to Restaurants 24 Hour Sup...

Three bedrooms, 4-7 Guests

Large, three bedroom apartment, 1,300 square feet, fully furnished, with a queen-size bed in the first bedroom, 2 twin beds in the second bedroom and two-twin beds in the third bedroom. There is a sitting area with table and chairs, kitchen and m...

Vacation Home Search

Find the perfect rental for your vacation