8 Labor Day Destinations For a Luxuriously Long Weekend

If you've been working hard all year, treat yourself to the three-day holiday getaway you've earned.

Can’t get enough fun in the sun? That makes two of us. It’s true that September marks the start of fall, but it also gives us our last true taste of summer, especially when Labor Day weekend rolls around.

Before the crisp autumn rolls in and the leaves start to change, end the hottest, longest season with a short but sweet trip to celebration. With the last days of summer in mind, consider adding one of these wonderful Labor Day getaways to your to-dos.

Toronto, Canada

Toronto skyline over water
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Visiting Toronto, Canada is consistently dubbed one of the best Labor Day vacays on earth. It all comes down to timing. For starters, you can catch the Canadian National Exhibition (better known as “The Ex”) from August 17 to September 3.

At this two-week extravaganza, you’ll be privy to air shows, carnival rides, parades, live performances, incredible food trucks, and local craft beers. Not to mention, you can typically find some seriously great flight deals for this time of year.

Cancun, Mexico

Beautiful shoreline view in Cancun,Mexico
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Give your summer a proper goodbye with a tropical getaway you’ll never forget. From its white sand beaches to its all-inclusive resorts, Cancun offers plenty of opportunities for visitors to breathe in the wonders of nature and manmade luxury all at once.

You may have some unusually great luck when it comes to booking flights and lodging. Bear in mind that September is famously Cancun’s rainiest month. But when the sun does emerge from the clouds, you’ll find plenty of reason to celebrate.

Read More: 5 Ways to Make the Most of a Rainy Beach Vacation

Vail, Colorado

wildflower covered mountain landscape in Vail during summertime
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Vail might be most known for its slopes, but summer and fall offer a completely different yet equally beautiful side to the landscape. Spend your Labor Day weekend picking wildflowers, hiking trails, and discovering stunning waterways.

Go tubing, take a gondola ride, go ziplining, and hop on the mountain coaster. If you’re looking for action, Vail is the place to be. Also, look into the Vail Valley Food Tour. You won’t be disappointed.

Read More: Top 7 Destinations For Adrenaline Junkies

Austin, Texas

Barton Creek Bridge spanning across the cold spring fresh clear waters of Barton Creek in Austin Texas skyline cityscape aerial drone view above green landscape Barton creek flowing into town lake
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There’s always tons to see and do in Austin, Texas. So unsurprisingly, Labor Day is fully loaded with fun for everyone. For instance, Austin’s citywide Free Day of Yoga falls on this holiday weekend. And the good food, shopping, art, and music options are practically endless.

Hit Lady Bird Lake and paddle around all afternoon. Hunt down free tickets to Sound & Cinema. Go on a camping trip and discover some of the best hikes in the state. Or just stroll around looking at jaw-dropping street art and trying out the food trucks. Whatever you do, ’tis the season for the most favorable weather in Austin.

Read More: Top Tips for Your Trip to Austin, Texas

Montreal, Canada

rainbow faces on brick wall in Montreal
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If you want a late summer, European vacay without going overseas, a long weekend in Montreal may be just the ticket. And during September, hotel prices drop and so does the temperature.

Picturesque and brimming with art, Montreal is an exquisite feast for the eyes. It’s also full of rich history and richer food. Here are 15 of the best things to do in Montreal, compliments of Tripadvisor.

Lake Tahoe, California

Aerial view of Lake Tahoe and the road around it.
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If you’re looking to relax alongside a scenic lake, set your sights on the north shores of Lake Tahoe. Whether you want to hike in the morning, sunbathe all day, or go kayaking in the glittering lake waters of Sand Harbor State Park or Donner Memorial State Park, this is one of the most idyllic Labor Day hotspots on the list.

And if luxury is what you’re after, book a few nights at The Ritz-Carlton, Lake Tahoe. It’ll give you plenty of reason to celebrate how hard you worked all year long.

Lexington, Kentucky

Raven Run Creek
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Calling all country music fans: make your way to Lexington, Kentucky for Labor Day weekend. You’ll arrive just in time to catch the star-studded Red, White & Boom music festival, featuring fireworks, food, and major recording artists like Luke Bryan and Blake Shelton. 

Beyond the city lights, you’ll have the chance to commune with nature at just the right time of year. In the world of fun festivities, The Bluegrass Classic Dog Show also falls on Labor Day weekend.

Oregon’s Wine Country

A vineyard showing yellow fall colors in September near Salem, Oregon
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Oregon’s Wine Country might be off your radar, but consider Labor Day Weekend the ideal time to change that. In September, the leaves of the Willamette Valley and Tualatin Valley change to a vibrant yellow and many tourists begin to leave.

Take advantage of the solitude, berries, apples, peaches, and late summer wine tastings before fall fully sets in. Go on a bike ride and breathe in the cascading lavender. Spending Labor Day weekend in Oregon’s Wine Country might not be wildest three-day weekend of your life, but it might just be the dreamiest.

Read More: America’s Best Wine Vacation Destinations

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