10 Places to Travel for Labor Day Weekend

Experience some of these sought-after destinations over the upcoming holiday weekend.

Our list of places to travel for Labor Day weekend includes something for everyone.

For many, Labor Day Weekend signals the end of summer. What better way to get one last taste of the season than a vacation? We’ve selected 10 of our favorite places to travel for Labor Day Weekend if you’re in need of a last-minute getaway:

  1. Summerfest | Milwaukee, Wisconsin
  2. The Ozarks
  3. Vail, Colorado
  4. Cape Cod, Massachusetts
  5. Wine Country | California
  6. Bourbon Country | Kentucky
  7. Mackinac Island, Michigan
  8. Austin, Texas
  9. College football games
  10. Panama City Beach, Florida

Keep reading and explore the destinations on this list for your own Labor Day Weekend travel inspiration. (Be sure to check local public health guidelines for hours and COVID-19 regulations.)

Summerfest | Milwaukee, Wisconsin

The World’s Largest Music Festival is back! Celebrate the end of the season at the first weekend of Summerfest in Milwaukee Sept. 1–4, 2021. The newly renovated American Family Insurance Amphitheater features Fall Out Boy, Weezer, Green Day, Luke Bryan, Chance the Rapper, and Twenty One Pilots over the first weekend of this year’s festival. Plus, dozens of other artists will headline the festival stages, including Cold War Kids, REO Speedwagon, Leon Bridges, and more.

The Ozarks

One of the South’s most popular summertime destinations, there’s plenty to do in the Ozarks — and plenty of ways to do nothing at all if relaxing is your goal. Go fly fishing or charter a bass fishing boat, watch for wildlife on a tram tour through Dogwood Canyon Nature Park, or sample upscale farm-to-table eats at rustic yet sophisticated restaurants.

Vail, Colorado

Forget snow and skiing! Summer and fall are a great time to visit Vail and explore the region’s scenic vistas, waterways, and hiking trails. Book a gourmet food, history, and art tour or explore the Betty Ford Alpine Gardens (the highest botanical garden in the country).

Cape Cod, Massachusetts

Cape Cod is the traditional destination for summer’s last hurrah. Soak up the sun on the beach, tour the bay on a boat, and enjoy fresh seafood at the fine restaurants or seaside shacks.

Wine Country | California

Wineries up and down the west coast are reopening to visitors — making wine country the perfect Labor Day getaway. However, many are open by reservation only, so it’s best to contact them early to confirm your spot for tours and tastings. While Napa Valley is probably the most famous wine region in California, Sonoma County also features impressive food and wine offerings and may be easier to book last minute.

Bourbon Country | Kentucky

For those who prefer whiskey to wine, late summer is prime time to tour Bourbon Country in the rolling hills of the American South. The Kentucky Bourbon Trail stretches roughly 60 miles from Louisville to Lexington, and you’ll find a unique blend of history and craftsmanship along with premium tastings.

Mackinac Island, Michigan

Michigan’s hidden gem is the ideal place for a last-minute escape. Take the ferry to this car-free haven where you can relax and enjoy the waterfront scenery, ride a bike (or a horse!), explore the cozy cafes and local shops, and sample the tastes of the island.

Austin, Texas

So much more than barbeque (though it is legendary), Austin also offers plenty of outdoor activities (parks, nature preserves, and hiking trails), historic districts, art galleries, trendy shops, and more. Spend your day exploring, grab a cocktail or try the local cuisine, then let your ears guide you — you’re sure to find a band you like in the Live Music Capital of the World.

College football games

NCAA football kicks off on August 28 and heats up with games throughout the holiday weekend all across the country. Show your school spirit and grab some seats at your local stadium or book a last-minute flight to root for your favorite team at an away game.

Panama City Beach, Florida

Catch some of country music’s hottest artists — including Chris Stapleton, Brooks & Dunn, Old Dominion, and so many more — at the Pepsi Gulf Coast Jam September 3-5, 2021. Superior is offering a limited number of exclusive corporate hospitality VIP suites to this event, complete with amenities like a private bar, unlimited drinks, and corporate branding. Contact us now for updated availability and booking information.

Need the expertise of Superior Executive Services? We can help you customize a getaway if your dream destination isn’t on our list of current sports, food and wine, or entertainment travel packages. To get started, contact us online or call 608.665.9070.

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