Fly’s 11 Best Labor Day Weekend Escapes

Sadly enough in a month is Labor Day, the unofficial end of summer. But, there’s still plenty of time to plan a sun-filled retreat and get that last trip in before the gloomy fall season takes over. To help you plan your getaway, we’ve put together Fly’s 11 Best Labor Day Weekend Escapes.

These are Fly’s 11 Best Labor Day Weekend Escapes:

Best Labor Day Weekend at martha's vineyard

1. Martha’s Vineyard, MA

Just a few miles off the coast, this high-falutin’ destination of the rich and famous offers exquisite views, fantastic shopping, and epic seafood. Our favorite thing to do is hit the fishing village of Menemsha and pick a restaurant to devour lobster and Clam Chowder. Be sure to attend the 22nd annual Labor Day Festival, where dozens of artists (local and international) come to show off their work.

Best Labor Day Weekend in new orleans

2. New Orleans, LA

Frankly this is a weekend destination at any time of the year, but over the holiday the city is hosting the 46th Annual Southern Decadence Festival. It’s essentially a massive LGBT party that brings in over 150,000 visitors from all over the world. Huge parades, block parties and concerts fill the town.


Best Labor Day Weekend in charleston

3. Charleston, SC

Visit one of the most historic towns along the East Coast for a weekend of great music at the Greater Charleston Lowcountry Jazz Festival. Now in its eighth year, come and join thousands of music lovers as they swoon to the melodies of Damien Escobar and Brian Culbertson, Jeffrey Osborne, Robert Glasper and more.

Best Labor Day Weekend in hawaii

4. Hawaii

For some reason flights to Maui and Oahu are at discounts we haven’t seen in years. This is peak summer and roundtrip flights from California are staying around $400 R/T. This time last year they were a minimum $200 more. We did a little research and found many resorts and hotels in Wailea and Kaanapali are also showing rates at over $100-$300 off.

Best Labor Day Weekend in dc

5. Washington, DC

There certainly is no shortage of things to see and do in our nation’s capital, from touring the White House, visiting the National Museum of American History, and relaxing on the steps of the Lincoln Memorial. Labor Day Weekend is a great time for music lovers to visit, with a free concert by the National Symphony Orchestra on Saturday and the Labor Day Concert at the U.S. Capitol on Sunday.

Best Labor Day Weekend in las vegas

6. Las Vegas, NV

It’s always a party in Sin City, but it’s one of the last chances to revel it up at the resort pool scenes. Most of these pool parties are more festive than the club scene at night. We recommend whatever resort’s pool you pick to attend, rent a cabana. You’re spending a lot of money anyway, so indulge with a few extra bucks. If you don’t rent a cabana we suggest you arrive early, as lines form quickly.

Best Labor Day Weekend in cannon beach

7. Cannon Beach, OR

Located on the beautiful Oregon coast, the small town of Cannon Beach offers ideal weather for an end-of-summer retreat. Gorgeous hiking trails in Ecola State Park, fascinating marine life, and the ultimate beach town experience make for one of the best labor day weekend destinations.

Best Labor Day Weekend at lake tahoe

8. Lake Tahoe

Beautiful, clear water ranging in different glistening shades of blue, Tahoe is the jewel in the crown of its two home states of Nevada and California. The water is warm even into late September and an extravagant fireworks display celebrates Labor Day. With many lake-side towns to stay in and visit, Lake Tahoe has no shortage of relaxation on or off the water.

Best Labor Day Weekend in sedona

9. Sedona, AZ

One of Arizona’s most beautiful destinations, Sedona is the ideal place to escape to. Surrounded by amazing natural features like the red-rock buttes, pine forests and canyon walls, it’s not hard to imagine why it is such a valued experience. The small town of Sedona offers plenty of ways to spend a day in the lively uptown or exploring the back-country of Arizona.

Best Labor Day Weekend in west virginia

10. New River Gorge, WV

The perfect close to an amazing summer is an even more amazing rafting trip on the New River Gorge River in West Virginia. Stay in a tent on the river, or a luxurious B&B in the woods near town. However you do it, you’ll spend your weekend in the great outdoors in one of the nation’s most beautiful landscapes.

Best Labor Day Weekend in vancouver

11. Vancouver, BC

The city of Vancouver is home to some of the most beautiful backdrops a city could have, and offers an incredible value for Labor Day getaways. Whether you take a leisurely stroll through beautiful Stanley Park, or soak up the history of Gastown, Vancouver is sure to delight both you and your pocketbook.

Start planning your Labor Day getaway with flights and hotels.

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