11 Labor Day Weekend Getaways to Start Planning ASAP

Plus, the best hotels and Airbnbs in each destination.

June 14, 2019

I'll never say no to a three-day weekend (or a day out of the office), but I always have mixed feelings about Labor Day. Yes, it's an excuse to take a road trip somewhere out of town or lounge around at the closest beach, but it also marks the beginning of the end of summer.

Because just a few weeks later, fall will arrive and the cool weather will slowly start to take over. Which means that those beach days and weekend picnics and outdoor dinners you've enjoyed the last few months are on their way out. So instead of staying home this Labor Day, I'll be making the the absolute most of the final, warm-weather days by taking a getaway to somewhere with plenty of sun, great food, drinks, and outdoor activities.

From a charming New England town in Maine where you can get your lobster roll fix to a historic, beachside destination in Bermuda, here are 11 Labor Day weekend trips you should start planning right now—before all the best hotels and Airbnbs get snapped up.

11 Best Labor Day Weekend Trips

1. Portland, Maine

Get your fill of all the New England summer classics—lobster rolls, beach walks, trips to the light house—in Portland, Maine. There are plenty of charming Airbnbs in the area, but we love the Press Hotel downtown for its boutique-style accommodations and vintage-styled rooms, each inspired by newspaper offices of the early 1920s.

2. Monterey, California

Photo by Monterey Bay Aquarium

Whether you're a fan of HBO's Big Little Lies or just want to spend the day strolling around the city's famous aquarium on the bay (don't miss the octopus feeding!), Monterey makes the perfect coastal escape. The nautical-themed Portola Hotel and Spa is set right on the waterfront, just a few-minutes' walk to the Fisherman's Wharf and downtown restaurants. Bonus: Monterey is just a short drive to nearby Carmel-by-the-Sea, Big Sur, and the Pebble Beach Golf Links should you want to take a day trip.

3. Mexico City, Mexico

Photo by Flickr/Carl Campbell

The Food52 team can't seem to get enough of Mexico City and it's not hard to see why: CDMX (Ciudad de México) is turning out some of the most exciting and delicious food in the world (from guava pastries to the best-ever tacos), not to mention it's sprawling neighborhoods and historic-meets-modern architecture.

There are so many cute Airbnbs to choose from (like this one with a stunning private terrace), but if you want to spend your Labor Day weekend indulging in a bit of luxury, nothing but the Four Seasons will do.

4. Asheville, North Carolina

Photo by Heather and Bob/Airbnb

If you prefer sweeping mountains and waterfall treks—and tasty Southern fare—head to Asheville, North Carolina. The city's home to a thriving arts district, a growing culinary and craft beer scene, live music venues, and is within driving distance of the grand Biltmore Estate and plenty of day hikes.

Book this cozy, contemporary cabin, complete with a fire pit and hot tub—just 10 miles outside of town to get that full-on rustic feel without sacrificing any creature comforts.

5. Park City, Utah

Photo by Montage Deer Valley

When you hear Park City, Utah, the first thing you probably think of is the star-studded film festival that happens every winter. But there's so much more to this charming mountain town than celeb spotting and skiing. Summer in Park City means mountain biking, fly fishing, and horseback riding. And the best part: the rates in the warmer months are at least half that (if not more) of what they are during the height of ski season.

To get the best of everything that Park City has to offer, stay at the Montage Deer Valley, which offers tons of activities, mountain-view accommodations, and one of the best spas in the area.

6. Portland, Oregon

Photo by The Nines Hotel Portland

If hip coffee shops, lush mountain greenery, and hey, even the Nike headquarters, sound like something you're interested in, opt for Portland, Oregon. We like The Nines Hotel downtown for its luxe accommodations and central location—the Portland Art Museum and the Japanese Gardens are within walking distance, while the Oregon Zoo is just a 15-minute drive away.

7. Austin, Texas

Photo by Lisa Hause/Iron Works Barbecue

According to Executive Editor Joanna Sciarrino, "Austin might be best known for its barbecue and tacos (and, damn, are they good), but it’s also so much more than that." Think: top-notch pizza, an excellent bar and live music scene, and plenty of quality bakeries and coffee shops to satisfy all your pastry and caffeine needs. The Guild Lavaca Street, an apartment-hotel complete with a pool, is a budget-friendly yet stylish outpost downtown—the ideal spot from which to explore the city.

8. Hilton Head Island, South Carolina

Photo by Lee Coursey/Flickr

If you're all about the beach, plan a trip to Hilton Head Island in South Carolina. This laidback island town is full of sun, sand, surf, wildlife (like dolphins and sea turtles!), and plenty of good golfing (if that's your thing) and it's perfect for families and couples alike. The Sonesta Resort is a popular option, thanks to its ocean views, two pools, and a free shuttle, but if it fills up before you're able to book, take a look around Airbnb—there are plenty of great options to be found.

9. Boulder, Colorado

Photo by Pixabay

Want to spend your long weekend in the happiest city in America? Then head to Boulder, Colorado. Set among the Rocky Mountains, Boulder is filled with jaw-dropping scenery (ever seen the Flatirons?), world-class biking and hiking trails, over 20 craft breweries, and all the laid-back vibes you could ever want in a vacation. For lodging, check out Basecamp Boulder right in downtown, where you'll find comfy, climbing-inspired lodging and a fire pit for roasting s'mores.

10. Delray Beach, Florida

Photo by Saltwater Brewery Delray Beach

Maybe I'm a bit biased (Delray Beach is where I grew up), but this laid-back Florida beach town makes the perfect sunny getaway. It's got a charming main street (Atlantic Avenue) packed with restaurants and bars, great local craft breweries (like Saltwater Brewery), and beautiful beaches. It's also just an hour away from both Miami and Palm Beach, making it the perfect base from which to explore South Florida.

When it comes to hotels, you can't go wrong with either the Marriott or the Seagate Hotel, as both are well-appointed and just steps from the beach.

11. Saint George, Bermuda

Photo by Go to Bermuda

Just under three hours by plane from New York City, the island of Bermuda makes a surprisingly easy-to-get-to destination for those in the Northeast. Once you get there, it's all about the ocean. The island's got some of the most beautiful beaches in the world, plus loads of water activities (think: snorkeling, boating, kayaking, and more. If you can snag a room before it fills up, stay at Aunt Nea's Inn in St. George, a historic bed and breakfast set on a UNESCO World Heritage site. Oh, and don't forget your Bermuda shorts.

Where will you be celebrating Labor Day weekend? Tell us in the comments below!

See what other Food52 readers are saying.

Erin Alexander

Written by: Erin Alexander

Erin Alexander is the Managing Editor of Food52.

1 Comment

stefanie June 15, 2019
Park City in the summer/early fall is super nice! My recommendation: stay in Park City, not at Montage, which is very, very isolated on top of a mountain the Deer Valley Mountain Resort and has a pretty mediocre restaurant. If you want to splash out money, the Washington School House Hotel is very cute boutique hotel in a restored schoolhouse. Rent some bikes - there's a nice, flat trail that heads out towards Kimball Junction or a bunch of mountain biking routes, do some hiking around Park City or out by Alta/Snowbird, and/or check out High West, Handle, Fletcher's, and other good eats on Main Street!