Four Unexpectedly Exciting Memorial Day Getaways for an Early Summer Road Trip

May 7, 2025

Seeking some solace from the busy city life? Tired of the rat race of punching time clocks? Need a break from your 9 to 5 without the long wait times at airlines? We’ve got you covered. You can reach each of these destinations with a reasonable and comfortable drive, making it a great start to the summer road trip list! We’re bringing you beaches, trails, forests, adventure, fun and plenty of sun right here in the middle of the good ol’ US of A. Forget about flight delays and REAL ID waitlines, you can hop in your new car from Classic right here in Waukegan, and be on the road to excitement, fun, and off to four unexpectedly exciting Memorial Day Weekend Getaways!

Starting off our list is South Padre Island off the southern portion of Texas. You’ll enjoy 34 miles of coastline and seemingly neverending sunshine with crystal clear gulf water! Known as the Sandcastle Capital of the World, you’ll have a truly memorable experience as you trek down the “Sandcastle Trail” – a beautiful collection of at least 30 sand sculptures created by local and global professional sculptures! The spectacular South Padre Island Birding Nature Center and Alligator Sanctuary takes birdwatching and nature appreciation to a whole new level; you and your family will love exploring the wildlife and ecosystems of the Rio Grande Valley and celebrating the unique creatures that inhabit this area through hands-on learning. The Port Isabel Lighthouse Historic Site is the sole remaining coast lighthouse in Texas open to the public, offering sweeping panoramic views of the coastline. South Padre Island Adventure Park offers a plethora of family-friendly activities including everything from horseback riding along the shores to zip lining, parasailing, and more. The Port Isabel Historical Museum offers a look into the history of the Mexican-American War through exhibits and historic artifacts, and is emblazoned with a custom painted fish mural from 1906. Book a private tour from the numerous local businesses and enjoy some parasailing, dolphin watching, nature trail walks, and more!

Headlands Beach State Park in Mentor is just outside of Cleveland, Ohio. This beautiful beach is a surprisingly beautiful getaway just outside the city limits with a large shoreline and surprisingly warm water of Lake Erie. The beach is vast and perfect for sandcombing as you search for brilliant sea glass, water-tumbled stones, and other shoreline treasures. This public beach attracts nearly two million visitors each year, and is perfect for swimming, picnicking, sandcastle making, fishing, nature watching, birding, and more. Of course, when you’re done with your beach day you can spend the rest of your MDW exploring nearby Cedar Point, Cleveland Aquarium, the Rock and Roll Hall of Fame, Great Lakes Science Center, or any of the many local Farmer’s Markets for some fresh, locally made and locally grown food.

North Beach in Racine offers an immense 50 acres of west-coast style beach day fun along Lake Michigan! Enjoy Zumba on the beach, live music all summer long, sand volleyball, and the best of the west coast without the long flight. It’s the ultimate summer oasis, perfect for a Memorial Day Getaway. This is another great family-friendly location with easy waters to navigate, a “Kids Cove” and playground area, and concessions bar with food and drinks. Plus, the area is the state’s first “Certified Blue Wave Clean Beach” – promising nothing but sparkling sand beaches and a pristine boardwalk for your enjoyment. Life guards are on duty in June through August, so swim at your own risk before season opener! Other attractions to enjoy nearby include the Racine Zoo, the Racine HarborMarket (now known as “HayMarket”), “Hot Summer Nights” concert series in the park, and First Friday fun will resume starting this month (May).

Telluride is an unexpected addition to the list, but we promise it’s just as fun in the “offseason” as it is during the Colorado winters. The town offers plenty of outdoor fun such as tubing, bungee trampolines, outdoor hiking, mountain biking, and Mountain Village Gondola rides. If you’re looking for the best fishing destinations and waterside fun, you’ll find it right there in the rocky mountains in any of the plentiful lakes, ponds, and alpine creeks by way of kayaking, stand-up paddle boarding, boating, and swimming. The summer months are known in the area as “festival season”; in May you can enjoy the Telluride MountainFilm Festival, followed by the Hot Air Balloon festival in June. You’ll also get a firsthand look at the beautiful history of the area at the Telluride Historical Museum or one of the local history walking tours!