Travel Tips

Labor Day Weekend Festivals Around the Country

Locations in this article:  Chicago, IL Louisville, KY San Diego, CA

Whether you’re hitting the road for Labor Day Weekend or staying close to home, there are festivals you can check out all over the country. This weekend, you can discover creations made by local artists, listen to jazz, learn more about Native American tribes at a powwow, and even watch a fireworks show…or three. Here’s our list of  can’t-miss Labor Day weekend festivals and events around the country.

36th Annual Chicago Jazz Festival


The Chicago Jazz Festival has been featuring top  musicians for over 35 years. Each year, rain or shine, artists and fans come together to take part in a huge musical celebration at Millennium Park. Make sure to arrive early since seating in the Pavilion and on the Great Lawn is available on a first-come, first-served basis.  The festival takes place from August 28 to 31.

62nd Annual Sausalito Art Festival


Upwards of 270 award-winning artists will show up for this open-air art event in Sausalito, California. Over the course of more than 60 years, the Sausalito Art Festival just keeps getting bigger, with an impressive following. There’s jury-selected artwork, but don’t  miss some of the special exhibitions, food, and drinks, while visiting the seaside village. General admission tickets are $25, with discounts for seniors and children 6 to 12 years old. Children under the age of five can attend for free. The festival takes place from August 30 to September 1.

12th Annual Louisville Worldfest


Looking for a little culture this Labor Day? Perhaps some authentic ethnic food from around the world? Then head for the 12th Annual Louisville WorldFest. Yes, you’re in Kentucky, but the mint juleps can wait—instead there’s food from Ethiopia, Jamaica, Thailand, and more. More than 90 artists perform on three stages, capped off by the Parade of Cultures and the Naturalization Ceremony, where hundreds of people take the U.S. oath of citizenship. Admission is free, and the festival takes place from August 29 to September 1.

North Carolina Apple Festival


Apple lovers know to head straight to Hendersonville, North Carolina this Labor Day weekend for the North Carolina Apple Festival. With approximately 200 apple growers in Henderson County, North Carolina has held the festival for over 60 years with freshly picked apples, arts and crafts, festival food, and free entertainment. You will also have the chance to watch the King Apple Parade. Just remember to leave pets at home, as they are not allowed. The Apple Festival takes place from August 29 to September 1.

27th Annual New Mexico Wine Festival

new mexico

With wine production dating back to the late 19th century, the New Mexico Wine Festival is a celebration of the rich history and tradition of wine making in the area—and to think that most folks don’t even know New Mexico is  a wine producing state. Over 15 wineries showcase their selections at New Mexico’s biggest wine festival. You can also listen to the live bands and participate in the hat contest. Actually, it’s better NOT to participate. Just watch! The festival runs from August 30 to September 1, and tickets start at $15 per day.

33rd New York State Festival of Balloons

Image Credit: Laura Mattatall

Image Credit: Laura Mattatall

The New York State Festival of Balloons is a great annual tradition. Up to 35,000 come every year. The festival hosts six scheduled launches, ranging from early morning to early evening. You can join the celebration with rides and games, tethered balloon rides, and much more. You should also experience the car show and arts and crafts at the Dansville festival. Admission is $5 per person and children under 12 years of age may attend for free. The festival takes place from August 29 to September 1.

Festival of Sail


If you love boats, then San Diego this Labor Day weekend is the place to be—at the largest Tall Ship festival on the West Coast. At the Festival of Sail, you can visit with the ships and crew, check out the beer garden, kids petting zoo, Naval war reenactors, and many more. You also have the chance to join a 30-minute bay cruise, complete with cannon battles. The Maritime Museum of San Diego and north Embarcadero transforms into a nautical theme park for the weekend—the festival takes place from August 29 to September 1. Tickets start at $7 per person.

Ashland Labor Day Powwow

A stream in Montana

Take part in a true cultural experience this Labor Day weekend at the Ashland Labor Day Powwow. You’ll have the opportunity to watch drummers and dancers from many tribes, and you can participate in gourd dancing and hand games. At the powwow, you can check out the food vendors as well as Native American art and beadwork, all while learning more about Native American culture. The Powwow takes place from August 29 to September 1.

10th Annual Bike Minnesota with Parks & Trails


Want a little physical exercise this labor day weekend? Minnesota’s Parks & Trails Council has organized a three-day riding tour. You will have the chance to learn about hydro-electric projects, railroad history, and geography while biking around Jay Cooke State Park. The tour comes with all meals and two daily rest stops with snacks. Additionally, David Minge, former Congressman and retired Minnesota Court of Appeals Judge, will be leading the event. The bike riding tour begins on August 29 and runs until September 1.

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By Justin Shamtoob for