Five Fun Columbus Day Weekend Getaways

Columbus Day is an underrated holiday. No one seems to remember when it is (the second Monday in October–this year, October 10), and although we know it commemorates Christopher Columbus’ arrival to the Americas in 1942, whether he actually deserves his own holiday remains highly controversial. However, Columbus Day provides the perfect opportunity to plan a fall getaway. The weather is usually quite lovely–for many areas, the second week of October marks the peak of fall colors–and many lucky kiddos have the day off from school.

columbus day weekend getaways

So before the gold and crimson leaves turn brown, take advantage of the long weekend. Here are five fun Columbus Day weekend getaways, all within driving distance of Lake County.

Columbus Day Weekend Getaways

Five Fun Columbus Day Weekend Getaways
A kayaker enjoys the fall splendor at Cave Point County Park in Door County, Wisconsin. Photo provided by Door County Visitor Bureau.

1) Door County, Wisconsin
Nestled on a peninsula between Green Bay and Lake Michigan, Door County is known for its pristine shorelines, expansive parks, quaint towns and striking fall colors. Check out Little Sweden Resort in Fish Creek, where you can rent a beautiful log villa and take advantage of the resort’s many amenities, including two indoor swimming pools, tennis courts and free bike rentals. Arrive on Friday for the “Friday at 4” wine and cheese party in the reception hall, followed by a bonfire and s’mores for the little ones.

Five Fun Columbus Day Weekend Getaways
Stroll along the shoreline or listen to bands perform at the Memorial Union Terrace along Lake Mendota in Madison, Wisconsin. Photo by Emily Mills for the Greater Madison Convention & Visitors Bureau.

2) Madison, Wisconsin
Madison is more than just a college town. The greater Madison area is home to 200 miles of hiking and biking trails and five lakes, where you can take a sunset boat cruise, rent kayaks or paddleboards, or simply enjoy an outdoor concert on the University of Madison’s Memorial Union Terrace. In the fall, check out the Dane County Farmers’ Market (the largest in the nation), which boasts 160 local producers that sell farm-grown fresh produce and specialty baked goods.

Five Fun Columbus Day Weekend Getaways
The dune buggy rides in Saugatuck, Michigan are fun for the whole family. Photo provided by the Saugatuck-Douglas Convention and Visitors Bureau.

3) Saugatuck, Michigan
Artists are drawn to Saugatuck’s pristine shoreline along Lake Michigan, expansive beaches and natural beauty. Known as the “art coast of Michigan,” Saugatuck has something for everyone–art galleries, boutiques, fine and casual dining, and a wealth of recreational opportunities, such as canoeing, paddleboarding, and sailing. Kids will love apple picking at a local orchard or the Saugatuck Dune Rides, where you can take a rumblin’ and tumblin’ ride across towering sand dunes.

Five Fun Columbus Day Weekend Getaways
The 2015 Galena Country Fair, a Columbus Day weekend tradition. Photo provided by the Galena/Jo Daviess County Convention & Visitors Bureau.

4) Galena, Illinois
Head to the Galena Country Fair during the Columbus Day weekend, where you can browse wares from more than 150 artisans and craftspeople from across the country, enjoy a farmer’s market with fresh produce and homemade maple syrup, dance to live bands, and delight your taste buds with fair favorites such as caramel apples, fudge and funnel cakes. Galena is also home to a number of art galleries, historical sites, and kid-friendly activities, such as horseback riding, zipline tours, and an alpine slide at Chestnut Mountain Resort.

Five Fun Columbus Day Weekend Getaways
The French Canyon in autumn at Starved Rock State Park in Oglesby, Illinois. Photo provided by the Starved Rock Lodge & Conference Center.

5) Starved Rock State Park, Oglesby, Illinois
With 13 miles of hiking trails, breathtaking canyons and waterfalls, and unspoiled natural beauty, Starved Rock State Park is a nature lover’s paradise. On Saturday and Monday during the Columbus Day weekend, Starved Rock offers Fall Colors Trolley Tours, which include a relaxing trolley ride, hot lunch, and guided hike to Council Overhang and Ottawa Canyon. On Sunday, October 9, be sure to check out the Burgoo Festival, where you can sample burgoo, a delicious, slow-cooked stew.

Are you planning a Columbus Day weekend getaway? Tell us where you’re going in a comment below!

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About Laura Otto 26 Articles
Laura Otto is an associate professor at Mount Mary University in Milwaukee, where she teaches courses in journalism, writing for new media and creative writing. She lives in Vernon Hills with her husband, Matt, and three kids: Cole (19), Maya (7) and Shane (4). When she isn’t grading papers or scrubbing crayon off the walls, she can be found playing Downton Abbey trivia games on Facebook or doodling all over her kids’ homework.

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