6 Getaways Perfect for Labor Day Weekend

Labor Day weekend marks the end of the traditional summer season but you still have room for one last trip! Not sure where to go? No problem, visit one of these six getaways perfect for Labor Day weekend.

Charleston, South Carolina


6 Getaways Perfect for Labor Day Weekend


It doesn’t take long after arriving in Charleston to see the broad appeal this harbor city holds. The large, walkable historic district is dripping in Spanish moss and feels like a step back in time. Visit one of the city’s many house museums or the historic city market to pick up a Lowcountry signature sweetgrass basket.

Within a short drive are multiple beaches. Choose from the laid-back ambiance of nearby Folly beach or the more elite Isle of Palms with its stately beachfront mansions. Charleston is also within an easy drive of many historic plantations. Visit Middleton Place with their distinct on-site inn and fine dining restaurant or walk the gardens at Magnolia Place.

Santa Cruz, California


6 Getaways Perfect for Labor Day Weekend


Located on the west coast of California, an easy drive from San Fransisco, Santa Cruz has much to offer the weekend traveler. Visitors will find beautiful beaches, redwood-covered mountains, and Natural Bridge State Park. Take a drive along the dramatic rocky coast for amazing views of the Pacific Ocean. Don’t forget to check out the beachside boardwalk and take a ride on the Big Dipper, a vintage wood roller coaster that’s been delighting visitors for over 90 years!

Portland, Maine


6 Getaways Perfect for Labor Day Weekend


Labor Day weekend is the perfect time to make a visit to Portland before the weather turns cold for the winter. This lobster-lover’s paradise has a thriving culinary, craft-brew and arts scene. You can also take time to relax at one of the waterfront restaurants on Commercial Avenue. After lunch, take a leisurely twenty-minute walk from downtown to nearby Crescent Beach to enjoy the sun and sand. If time allows, try a whale watching trip to search for humpback whales, it’s the perfect way to end the summer.

Chicago, Illinois


6 Getaways Perfect for Labor Day Weekend


Travelers looking for an endless supply of things to do need to look no farther than Chicago.  From food to art, festivals abound in Chicago over Labor Day weekend. If you love music, head to the Chicago Jazz Festival at Millennium Park or the North Coast Music Festival at Union Park. Foodies will love the Great American Lobster Festival. You can also head over to Jefferson Park for a Taste of Polonia, a Polish-inspired food festival. After getting your fill of the festivals, head over to Navy Pier for music and the area’s largest fireworks display over Labor Day weekend.

Sarasota, Florida


6 Getaways Perfect for Labor Day Weekend


In addition to gorgeous beach and crystal clear water, Sarasota has tons to do over Labor Day weekend. Take in the Sarasota Sailing Squadron’s annual regatta with sailors from the US and Canada. Take in the 61st annual Pioneer Days festival with everything from car shows to boat races. Or, head to nearby Venice for the Venice Triathlon or Venice Crafts Festival. Be sure to end your days at the regions many fine seafood restaurants.

Washington, DC


6 Getaways Perfect for Labor Day Weekend


Finally, what better way to spend your Labor Day weekend getaway than taking in the many monuments and museums in our nation’s capital? Family attractions like the National Zoo and Air and Space museum make this a huge hit for travelers with children. The kids will love taking a paddleboat ride around the reflective pond in front of the Jefferson Memorial. For those traveling without children, Washington’s thriving club, restaurant, and bar scene will not disappoint.

Don’t love any of these options?  Perhaps a trip to Los Angeles is more your style!  You can even try one of these four luxury day trip ideas from Los Angeles.

Suggested For You

What to wear when traveling

Look Chic When Traveling

Do you struggle with what to wear when traveling?  Kristen Taekman is sharing her favorite tips for traveling and arriving at your destination in style.

6 Getaways Perfect for Labor Day Weekend