Last-Minute Trip Ideas to Make Great Memories This Labor Day Weekend

Hotel property near Golden Gate Bridge
Courtesy Image

Is this your situation? You promised yourself—and others—that 2022 would be the year those great Labor Day Weekend plans were actually, y’know, planned months in advance. Now, with less than three weeks to go, here you are, yet to lift a finger or click a mouse for a hotel reservation. If that’s the deal, you came to the right place. Here are a dozen epic, last-minute trips to book for Labor Day Weekend, whether you’re craving mountain adventure or a cosmopolitan escape.

Asbury Ocean Club in Asbury Park, NJ
Nikolas Koenig

1. Asbury Ocean Club in Asbury Park, NJ

This LDW, head to this gorgeous oceanfront retreat in the artsy, thrumming town of Asbury Park. Yes, the same one where Bruce Springsteen launched his career. There’s a big surf culture here, so bring your board if you skip waves, or just pack a few books to enjoy from the pool deck with a stellar view of the Atlantic. To celebrate summer’s sweet conclusion, catch Motown greats, the Commodores at Asbury Lanes, September 2, or check out Gotham Smash Burger x Asbury Brewing Company September 3 at Asbury Ocean Club’s sister property, The Asbury Hotel (from $695/night) for juicy burgers and hoppy brews. A leisurely stroll along the nearly 130-year-old boardwalk doesn’t disappoint, nor does a jaunt to The Stone Pony’s outdoor stage and beer garden.

Looking for a trip down the shore later in September? Book your stay around the Full Moon Party at The Asbury Hotel (September 9-11). This woo-woo fest will be led by celebrity psychic medium Sarah Potter, and includes a Full Moon ceremony under the stars, complete with night swims and live tunes.

[From $1,079/night; asburyoceanclub.com]

Chebeague Island Inn in Chebeague Island, ME
Chebeague Island Inn

2. Chebeague Island Inn in Chebeague Island, ME

The lure of Maine peaks in late summer, and this bucolic retreat is where you want to spend your holiday weekend enjoying it. Perched on Casco Bay—a short water taxi ride from Portland—prepare yourself for a summer camp throwback in the remote backcountry of coastal Maine. Under the resplendent shade of two-and-a-half acres of trees, play cornhole, bocce ball, croquet, badminton, volleyball, or ladder toss—or all of ‘em (available by request at the front desk). The inn also has you a stone’s throw from biking and hiking trails on craggy coastlines, sandy beaches, tennis, golf, and fishing excursions.

If you want to get your craft beer fix, transportation to and from Portland is provided upon request for swinging by a brewery or two. When you’re ready to relax, nothing beats lazing in an Adirondack chair with a “Sunset Landing” cocktail and appetizer menu, or lounging on the porch for the designated “Summer Reading Hour.”

[Starting rate for September 1 is $299, with a minimum three-night stay for LDW; chebeagueislandinn.com]

The Rosewood Washington, D.C. hotel in Washington, D.C.
Rosewood Washington D.C.

3. Rosewood Washington, D.C.

There’s something about D.C. in the summer. If you’re looking for a city getaway here, set your sights on this winning hotel, complete with 55 superb accommodations including the city’s first standalone Townhouses (from $1,900/night). Spend your long weekend at the rooftop pool with the city skyline glimmering in the background and noshing at the property’s CUT by Wolfgang Puck or CUT Bar and Lounge. Before you skip town, book a Potomac River Cruise through the hotel. The private water tour includes a picnic lunch from the CUT culinary wizards.

[From $700/night; rosewoodhotels.com]

The Reeds at Shelter Haven in Stone Harbor, NJ
The Reeds at Shelter Haven

4. The Reeds at Shelter Haven in Stone Harbor, NJ

There’s no shortage of natural draws to this singular Jersey Shore hideaway—starting with a private boat charter right from the hotel’s docks, where kayaks, stand-up paddleboards, and more are at the ready. Then it’s on to the property’s Salt Spa for flotation therapy or a massage. Beachfront fun here inludes complimentary daily beach service in a chauffeured electric car, followed by a bayfront meal at Water Star Grille. Downtown is brimming with small-town shops, perfect for browsing pre-beach and/or after your 8 a.m. yoga class on the roof garden sun deck (included with your stay). You may only be 90 minutes from Philly or two hours and 45 minutes from NYC, but otherwise these breezy, luxury resort digs are a world apart.

[from $595/night; reedsatshelterhaven.com]

The Montauk Point Lighthouse
Discover Long Island

5. Montauk, NY

It’s off to “the end of the world” you go to celebrate the unofficial end of summer. During your stay, embrace Montauk’s famous surf culture, gaze at the scenic bluffs, and swing by the Montauk Point Lighthouse, commissioned by President George Washington in 1792. Other items on your itinerary should include TailWrapped Sportfishing for an off-shore fishing charter and Montauk Brewing Company for a tipple. To “rough it,” camp out on the beach at Hither Hills State Park or stay in renovated motel-style accommodations at Hartman’s Briney Breezes Beach Resort (from $495/night).

Gurney's Montauk Resort & Seawater Spa
Gurney’s Resorts

We’d be remiss not pointing you towards Gurney’s Montauk Resort & Seawater Spa (from $1,025/night)—featuring a newly revamped spa with the only ocean-fed seawater pool in North America, plus indoor-outdoor treatment rooms overlooking the Atlantic Ocean and a eucalyptus steam room. Otherwise, post up on the resort’s 2,000-foot stretch of private beach in a daybed or lounge sofa before heading to Scarpetta Beach for fresh catch like seared scallops, charred octopus, and branzino.

To learn more, visit montaukchamber.com.

Cavallo Point in Sausalito, CA
Cavallo Point

6. Cavallo Point in Sausalito, CA

The Bay Area is spoiled with some of the best weather of the year come September, and this bayfront lodge is a fine option to spend the last of your summer Fridays. Tucked off the northern end of the Golden Gate Bridge within the Golden Gate National Recreation Area, you’ll be surrounded by a soul-restoring 75,000 acres of national parkland filled with some of the most gorgeous hiking and biking trails in the Bay Area. Try hiking from the ocean to the top of Montara Mountain at Rancho Corral de Tierra if you have a half-day or more.

For a longer journey to Muir Woods or Rodeo Beach, grab one of the hotel’s in-house Lexus vehicles for the day—or hop on a complimentary vintage e-bike to wander around Sausalito. When your sore Achilles needs a break, book a treatment at the property’s Healing Arts Center & Spa for a massage or cupping treatment.

[from $499/night; cavallopoint.com]

Kenoza Hall in Kenoza Lake, NY
Lawrence Braun

7. Kenoza Hall in Kenoza Lake, NY

Make it a Sullivan County summer for the books at Kenoza Hall, an idyllic lakefront property about two hours from New York City. They’ve got aerial yoga, a pool, barrel sauna, and the stellar Hemlock Spa—plus the recently unveiled group of ten luxury accommodations that’s a hat tip to the late-19th-century bungalow colonies in the Catskills. Should you choose to leave your bloody mary and moules frites lunch from the property’s restaurant patio, head to Roscoe, just a few minutes away. Anglers and imbibers alike will adore “Trout Town USA,” thanks to streams galore and Do Good Spirits, Roscoe Beer Co., and The Junction.

The DeBruce hotel
Lawrence Braun

During your trip, be sure to make a reservation at The DeBruce, a hotel and restaurant in nearby Livingston Manor for a memorable multi-course tasting menu ($225 per person). It’s well worth the pretty penny, with innovative dishes like trout consommé, chicken liver with saltines (an homage to original Polish and Jewish communities from the Catskills’ heyday), and chocolate made with burned bread and pine ice cream with sorrel, gooseberry, and maple. The property has a private trail system and private fly-fishing. A few, winding miles away, Upward Brewing is located on a public park with hiking trails and a mountain nicknamed “Beer Mountain”—for enjoying that mile-high brewski.

[from $544/night; kenozahall.com]

PGA National Resort in Palm Beach, FL
Will Pryce

8. PGA National Resort in Palm Beach, FL

Golfers, this one’s for you. Venture to the newly transformed PGA National Resort, which reopened last spring after a $100 million renovation. The spectacular property now features a pair of new golf courses, a new restaurant collection, and a spa designed by Venus Williams’ V Starr (the tennis pro’s first spa). During Labor Day Weekend, guests receive the special offer of 15% off accommodations, a $75 resort credit, and complimentary self-parking. When you’re not on the The Palmer or The Estate course, play tennis or pickleball, or feast at The Butcher’s Club or Honeybelle.

[From $260/night; pgaresort.com]

Brasada Ranch in Powell Butte, OR
Brasada Ranch

9. Brasada Ranch in Powell Butte, OR

Itching to scratch Oregon off your list? A voyage to Brasada Ranch is a good place to introduce yourself to the Beaver State. Located just a half-hour from Bend, the luxury ranch’s cinematic views of the Cascade Range are your backdrop here. Pamper yourself with Labor Day weekend offerings like horseback riding to the top of Spirit Rock or a nature walk, guided meditation, and yoga with jaw-dropping high desert views. Once you’re all sweated up, cool off at the adults-only pool, which will be playing tunes and serving up craft beers and local wine by Silver Moon Brewery and Treasury Wine Estates. Close out the day at Brasada’s Feast From The Fire, showcasing a three-course family-style meal with ingredients from local farms and live music from beloved regional acts.

You can spend your days on these sprawling 2,000 acres golfing, hiking, fishing, biking, playing volleyball, shooting hoops, or just lounging at one of the many fire pits around the property with new friends or old. Accommodations here run the gamut from lodge suites to cabins.

[From $399/night; brasada.com]

Hyatt Centric Beale Street Memphis in Memphis, TN
Hyatt Centric Beale Street Memphis

10. Hyatt Centric Beale Street Memphis in Memphis, TN

It’s high time you visit Memphis. Make Hyatt Centric Beale Street your home base come early September, which first welcomed guests in spring 2021 as the first and only hotel to be on legendary Beale Street. For LDW, on Friday night, enjoy canoes + cocktails at Shelby Farms Park. Then, on Saturday, rock out to the Doobie Brothers at Live At the Garden. If you still have energy, Sunday, September 4 is the 4th Annual River City Jazz and Music Festival—which pairs well with a pre-concert distillery tour at nearby Old Dominick or an outing to Grind City Brewing, just a short drive from the property.

Other must-visits include live music at BB King’s and a fancy dinner at speakeasy Itta Bena (up the fire escape above BB King’s), and a BBQ ribs spread at Rendezvous. Of course, you’ll have to drop by Elvis’ home, Graceland, and visit the National Civil Rights Museum. If you can, spend an afternoon at one of the Memphis River Parks. Our vote is Mud Island or Greenbelt.

[from $239/night; hyattcentricbealestreetmemphis.com]

The Foundry Hotel in Asheville, North Carolina
The Foundry Hotel, a Raines managed property

11. The Foundry Hotel in Asheville, North Carolina

Asheville is a town right after our sensibilities: great beer, great mountains, great people. Nestled in the Blue Ridge Mountains, pack your hiking boots for long days experiencing the grandeur that is Great Smoky Mountains National Park—and your flip-flops for a smattering of microbrewery tastings. Asheville has one of the highest numbers of breweries per capita in the entire country. Make The Foundry Hotel, housed within the city’s old steel foundry, your home away from home. The hotel offers one-on-one neighborhood tours with an on-site historian, a Tesla Model X house car to take a spin on the scenic Blue Ridge Parkway, and an onsite restaurant Benne on Eagle which doles out critically acclaimed Appalachian cuisine.

The big (as in humongous) don’t-miss attraction in these parts is the Biltmore Estate—the largest private residence in the U.S. Chill out afterwards with a Picnic in the Block Experience on the property’s great lawn via the hotel’s partnership with Dreamscape Luxury Picnics. For more tips on where to climb, bike, hike, and brewery hop, check out our guide here.

[From $572/night; foundryasheville.com]

View of the Minneapolis skyline
Explore Minnesota

12. Twin Cities, MN

Minnesota in September is always a good idea. The Twin Cities of Minneapolis and St. Paul have some incredible urban greenspaces, superb craft beers, and lakes, lakes, lakes. There are 11,842 of them in the state. Hop on a bike and push your pedals along the Twin Cities’ portion of the Mississippi River Trail as it follows the mighty river from north Minneapolis to downtown St. Paul and beyond. We’re also drawn to voyages along the Midtown Greenway, a 5.5-mile former railroad corridor bike highway for south Minneapolis, and a traipse through the amazing House of Balls art gallery.

The famed Mall of America is currently celebrating its 30th anniversary, if tax-free shopping beckons you indoors. When it comes time to call it a night, our top two choices are Hewing Hotel (from $300/ night), located in the thrumming North Loop neighborhood of Minneapolis, and St. Paul Hotel, one of the “Historic Hotels of America” (from $199/night).

To learn more, visit exploreminnesota.com.

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