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Labor Day Weekend Entertainment

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By Madeline Klein on August 24, 2021 in Travel

Labor Day is recognized as the unofficial last day of summer. If you decide to travel, Say Insurance® has plans for your Labor Day and we have kept in mind how important it is to social distance. This list will give you something fun to do for the holiday in each of our Say states.


Take a stroll down Chicago Lakefront Trail. If you are looking for something fun to do with the whole family while keeping your distance, this is a great choice. Be prepared to keep it moving though! The Chicago Park District says the trail can be used for commuting and exercise from 6 AM to 7 PM, as long as you’re in constant motion. Hey, that might be the motivation we all need while running!

Looking to spend the weekend under the stars? Look no further than the harbors at Lake Michigan! The best part is you don’t have to own your own boat. Get My Boat’s website has yachts, party boats, and more that you can rent by the hour. If you want to feel extra fancy, some of these even come with your very own captain. Trip Advisor has recommendations for other boat rentals across Chicago if you’re looking for a speed boat or pontoon instead. Either way, yell “All aboard” and hit the water this Labor Day!


Your opportunity for the condensed Colorado experience is the weekend of the Taste of Colorado festival. This Labor Day event brings people from all over the country to indulge in local food and drinks. Located in Denver, CO, the festival is a fun way to get the whole family out of the house for the weekend. During this event, vendors from all over the city bring their most popular menu items for you and your family to try. Come enjoy exceptional food, local breweries, live music, arts, crafts, and more!


Being the music capital of the US, you are bound to stumble upon some jamming music festivals over Labor Day weekend. But if music and festivals are not your thing, and you would rather enjoy the day relaxing, take a stroll through one of Nashville's bountiful parks. From Centennial Park to Nashville’s Greenways, you’ll find plenty of nature to explore! While you’re out and about, leave the cooking to somebody else. Nashville provides options galore with restaurants serving hot dogs, pizza, and world-famous bbq! This is a great opportunity to grab take-out and watch your favorite movie after a long hike.


St. Louis is a city with plenty to do and see. Check out some of the family-friendly destinations like Grant’s Farm, St. Louis Science Center, or St. Louis Zoo. The zoo is a must-see while in Missouri and with free admission, it’s well worth a day trip to see the giraffes and zebras (okay, maybe those are just our favorites). Don’t forget to check their safety recommendations and make a reservation ahead of time!


If you are looking to participate in a race this Labor Day weekend then Bike For the Brain is the event for you. Hosted in Mission, Kansas, bikers hop on their bikes and pedal to their heart’s content. The event has 4 tiers ranging from 3 to 65 miles. The proceeds go to Kansas City area agencies that enhance the lives of people with mental health disorders. Their goal is to raise awareness for mental health while erasing the stigma that surrounds these disorders! You can participate as a cyclist, sponsor, community partner, volunteer, Walk for Recovery participant, or Recovery Information Exchange participant.


Indiana hosts many fairs and festivals over Labor Day weekend. If you're looking for something fun to do with your family, check out the Labor Day Celebration in Princeton, or the Ligonier Marshmallow Festival. No matter what part of the state you're in, you're bound to have some fun checking out the local celebrations!

As the nation starts to open up again, we’re hopeful you will find some fun and safe activities to finish out your summer. If you’re driving to enjoy your Labor Day weekend, make sure you’re covered with Say Insurance®!

Madeline Klein is Say's Digital Content Producer. She graduated from the University of Missouri with a Bachelor of Journalism, emphasis in Strategic Communication. Her experience is in writing and digital media. Madeline loves using her creativity to write and design new and exciting pieces of work for Say!