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Labor Day Weekend Entertainment

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By Madeline Klein on August 14, 2020 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.


The Chicago Park District decided to reopen the 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, as part of their reopening plan, said 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? Lucky for you the harbors at Lake Michigan are open! The best part is you don’t have to own your own boat. Get My Boat’s website has yachts and party boats galore 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 all 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!


Due to COVID-19, many of this year’s events are cancelled in Tennessee. If you’re having trouble deciding what to do, but know you want to 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 land 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.


If St. Louis was the original plan, but your go-to Grant’s Farm is closed for safety reasons, schedule an appointment at the St. Louis Zoo. It’s 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). You’re required to wear a face covering, so even though the animals can’t see you smiling – it’ll be worth it to see the Big Cat Country and Fragile Forest exhibits. Don’t forget, you have to register in advance for a time slot!


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.

Although, COVID-19 has cancelled many of our summer events, we’re hopeful these will take place. If you’re driving to enjoy your Labor Day weekend, make sure you’re covered with Say Insurance®!

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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!