18 Easy Labor Day Trips from New York, Los Angeles, Austin, San Francisco and Chicago

Head out of the city for a bucolic country weekend along the Hudson River by car or Metro North Rail. The Hudson Valley is dotted with scenic national parks, where you can hike to refreshing swimming holes, and charming small towns, where you can shop (and eat) your way down main streets. Check into a recently refurbished room at the Hasbrouck House in Stone Ridge, and make your way to Woodstock for tacos al fresco at Tinker Taco Lab and local ice cream at Nancy’s of Woodstock. Take a culture break at the Dia: Beacon and the newly opened Magazzino Italian Art.

Two hours from NYC, Philadelphia holds both historical sites and cutting-edge dining. Swing by the Liberty Bell and Independence Hall on your way to shop the small boutiques of Old City. Fortify with breakfast at Federal Donuts before getting your cultural fix at the famed Philadelphia Museum of Art (yes, you can do the Rocky pose at the top of the stairs) and impressionist masterworks at The Barnes Foundation. For dinner, try for a reservation at local favorite Vernick Food & Drink (a 2017 James Beard-winner for Best Mid-Atlantic chef) or gourmet vegan restaurant Vedge.

A flight is an option here (it’s only an hour), but this is also a doable road trip. Portland offers cooler weather, endless lobster rolls and great craft beer. Start your day with a morning bun at Standard Baking Co. before you head for a tour of the Allagash Brewing Co. Cruise around the town on a bike rental to the Peaks Island ferry, where you can easily spend an afternoon house-gazing (stop for an ice cream cone at Down Front before you board your return trip). Wind down with cocktails and butter-soaked oyster rolls at Eventide or settle in for fine dining at Fore Street.

The North Fork offers a more relaxed, pastoral option to its southern Long Island neighbor, the Hamptons. Set out sailing in the bays, or let someone else steer with a short ferry ride to Shelter Island, where you can spend a day on pristine beaches. Greenport provides a good base for exploring the area, as well as hotel options like The Harborfront Inn. Take your pick of wineries to visit. Rosé lovers will love the Croteaux vineyards, while Shinn Estate Vineyards specializes in biodynamic varieties. If you want to indulge at dinner, stay (and eat) at the perennially popular North Fork Table & Inn.

Roughly 90 miles away from LA, you’ll find the laidback, boho retreat of Ojai. Treat yourself with a stay at the Ojai Valley Inn & Spa, where you can retire for an aromatherapy massage after hiking in Los Padres National Forest. Eat breakfast at the family-run KNEAD Baking Company before shopping at town favorites including Bart’s Books, Tipple & Ramble, and Summer Camp. Pick up local produce like citrus and olives from the groves, along with a bottle or two from Ojai Olive Oil. And go for ultimate rejuvenation by simply soaking at the therapeutic Ojai Hot Springs.

Make like you're joining the Rat Pack with a trip to mid-century modern haven Palm Springs. Hotels like The Parker Palm Springs and The Ace Hotel & Swim Club wink knowingly at the established design aesthetic of the city while giving it an update. Indulge in Palm Springs past with vintage shopping on N. Palm Canyon Drive, with stops at Cheeky's for all-day breakfast and dinner at the upscale Workshop Kitchen + Bar. Finish the weekend with the Palm Springs Modern Tour of iconic architecture and an escape into a desert landscape at the Moorten Botanical Garden and Cactarium.

There’s more to Las Vegas than gambling. Boldface chefs from around the world have opened up over-the-top restaurants, including L'Atelier de Joel Robuchon, Jaleo (José Andrés), Bouchon Bistro (Thomas Keller), and Restaurant Guy Savoy. Take a break from the glitz with a trip downtown to see The Neon Museum and a snack break at Carson Kitchen, or head to nearby Red Rock Canyon for a hike through an otherworldly landscape.

Easily accessible by ferry from Long Beach, San Pedro, and Dana Point, this channel island is a mix of resort towns, beaches and nature trails. Land in the main town of Avalon, and drop your luggage before heading for a hearty breakfast at Original Jack's Country Kitchen. Settle in for a day of sand and sea at the Descanso Beach Club, a private beach with public access where you can get your lunch delivered to your chair. After strolling the boardwalk, have a sophisticated dinner at Avalon Grille. The more adventurous can go for hikes on the Trans-Catalina trail and even zipline.  

Just outside of Austin city limits, the hipster urbanity gives way to green hills dotted with resorts, wineries, small towns, and yes, plenty of Texas BBQ. Golf courses are plentiful, with the Tom Fazio-designed Fazio Canyons topping golfers' must-play lists. With over 50 wineries, the Texas Wine Trail is clustered around a series of small, historic towns like Fredericksburg, New Braunfels and Kerrville. The Salt Lick BBQ has been a Hill Country institution for fifty years (and you’ve probably seen photos of its legendary pit), but other options include Hayes County Barbeque and Cooper's Old Time Pit Bar-B-Que.

Less than a three-hour drive away is Houston, one of the country’s most diverse metro areas. James Beard winner Chris Shepherd blends culinary cultures at his restaurant Underbelly, but more traditional versions can be found for almost any cuisine: authentic pho at Pho Binh, creamy chile con queso at Ninfa’s on Navigation, and brisket worth waiting for at Killen’s Texas Barbeque. Pass the time between meals at outstanding museums including The Menil Collection, The Museum of Fine Arts Houston, and the Contemporary Arts Museum Houston. Or cool off while shopping at the mega-shopping center The Galleria, with 2.4 million square feet of space (everything’s bigger in Texas, right?).

San Antonio is the closest big city to Austin, but worlds away in terms of ambience. You can’t miss the Riverwalk, whether to stroll through the picturesque sidewalks or stop for dinner at one of the many cafes lining them. Originally built in 1894 as Pearl’s Brewhouse, Hotel Emma is a high-style addition to the hospitality scene, offering creative American dining at Supper. But San Antonio’s particular addition to the culinary lexicon is the puffy taco, which was introduced (and still served) by Ray’s Drive Inn, which opened in 1956. And for some of the best and most interesting Mexican food in America, see if you can get in to Mixtli, the tiny 12-seat restaurant from 2017 Best New Chefs Diego Galicia and Rico Torres.

Nothing says long weekend like a family-friendly beach trip. The sandy shores and warm Gulf water of southern Texas don’t disappoint with over 100 miles of beaches. The Padre Island National Seashore offers everything from windsurfing to fishing to baby sea turtles viewing (or just soaking up the sun). Get even more wildlife into your weekend at the Texas State Aquarium, which includes exhibitions on sharks, sting-rays, and an outdoor splash pad for the kids. Take in views of the city while having a high-end, high-floor dining experience at Republic of Texas Steak House.

Yes, you certainly know about Napa, but September is as good a time as any to go. With hundreds of wineries and plenty of delicious food it’s hard to go wrong. Do call ahead to reserve your spot at your selected tasting since holiday weekends are busy. Eat your way through Yountville, which ranges from the hard-to-reserve (Ad Hoc) to the more casual (pizza at Ciccio or Redd Wood). Tap into your adventurous side with hot air balloon rides and bike tours between the wineries.

Thanks to massive mudslides and a washed-out bridge, parts of the famed Pacific Coast Highway drive are closed, but it’s still possible to visit Big Sur with some careful planning. The stretch north of the Pfeiffer Canyon Bridge is drivable so you can check out the sea lions and the iconic lighthouse at Lighthouse Field State Beach. The Julia Pfeiffer Burns  Big Sur State Park is open with some specific trails and areas still closed to the public (check for updates on the park’s Facebook page). Plan for dinner in Carmel by the Sea at French charmer La Bicyclette or the envelope-pushing Aubergine.

Your first decision is which side of Lake Tahoe do you prefer to stay on: the quieter, more nature-focused North shore or the more boisterous, fun-loving South shore? You can enjoy water sports on either side, including jet-skiing, parasailing, boating, and kayaking. And eating with a lakefront view goes without saying at restaurants like Christy Hill and Lone Eagle Grille. And if you don’t want to go back home empty handed, make sure to check out the shopping at stores like Bespoke in downtown Truckee (with a stop for the truffle fries at Moody’s).

Lake Geneva has been a popular getaway for Chicagoans since the 1850s, when wealthy industrial barons built grand vacation estates. You can now walk by the stately homes on the waterside Shore Path, which stretches for some 20+ miles. For another slice of history, join the U.S. Mailboat for a scenic tour while actually delivering the mail around the lake. Play a round of golf at one of three masters-designed courses at Geneva National and stay for outdoor drinks at the neighboring Ridge Hotel's BAR 55 on the Veranda. Hang with the locals at Sprecher’s for pub food and Wisconsin-brewed beers.

Welcome to Beer City USA. Tailor your visit around tours of 60+ local breweries, including Founders Brewery, HopCat and Brewery Vivant (which also serves full meals). Grab breakfast at Field & Fire before taking advantage of the down time by fishing in the Grand River or perusing the vendors at the Downtown Market. Enjoy art and nature simultaneously at the Frederik Meijer Gardens & Sculpture Park, and visit a carefully restored Frank Lloyd Wright prairie house at the Meyer May House. Finish off your stay with a farm-to-table meal paired with sustainable wines at Grove.

Take in nature from the northern shores of Lake Michigan’s Grand Traverse Bay—a longer (5 hours) but still doable drive for the long weekend. It's worth the effort the magnificent views from Sleeping Bear Dunes National Lake Shore towards Lake Michigan. You can go for a totally different kind of trail with The Leelanau Peninsula Wine Trail, with three different options of loops to follow for tastings at local wineries. Inside the city, explore the shops and eateries at Warehouse MRKT or the Village at Grand Traverse Commons. Traverse City is known for hosting the National Cherry Festival, and you can visit the original location of the Grand Traverse Pie Company for their hallowed take on cherry pie.