11 Best Places to Travel for Labor Day Weekend

There’s nothing better than traveling to an unknown town, moseying into a low-lit bar, and striking up a conversation with a stranger—only to find out they grew up there, raised their kids there, and have plenty of nearby recommendations to reveal. 

Or maybe you stumble into your hotel lobby and encounter a concierge with years of knowledge about the city. Within a few minutes, you’ve got a plan for avoiding the tourist traps and instead, one for heading off the beaten path. 

That’s the spirit of our Insider Guides, where we gather up secret travel tips from local experts in some of the top destinations around the West. Ahead of Labor Day Weekend, we rounded up some of their top itineraries, chock full of insights for making the most of your trip. Happy traveling!

Homer, Alaska

iStock/Getty Images Plus

Emma Teal Privat and Claire Neaton are no strangers to fishing boats. The sisters grew up wild harvesting with their family in Alaska’s Aleutian Islands and now helm an all-woman team that provides fresh sockeye salmon, Pacific cod, and more delivered right to your door. They’re headquartered in Homer, on the south side of the state, so we asked for their recommendations in and around the Kenai Peninsula. Read their full guide here.

Carlsbad, California

Delainy Reinard

A fourth-generation Carlsbad resident, Robyn Ukegawa has been involved in her family business, the Carlsbad Strawberry Company, for years. You can go into the strawberry field and pick your own fruit, or wander through the corn maze for cute photo ops. Ukegawa also has other tips for exploring the city known for its beaches and breakfast spots. Read her full guide here.

Napa, California

Demeine Estates

George W. C. Walker III was just looking for an internship when he emailed Wade Cellars, the Napa wine label by former professional basketball player Dwyane Wade. He didn’t expect to receive an offer to become the brand’s first full-time employee, but that’s exactly what happened. So, shortly after Walker launched a series of Graped Out wine tastings in the Midwest to make vino more accessible to people from all walks of life, he moved to Napa. He’s since helped Wade expand into more than 40 states with a goal of “inclusivity and accessibility, first and foremost,” Walker says, “and creating dope juice.” Here are some local favorites around the brand’s home base.

San Francisco, California

Laura Drake/Getty Images

Meenal Patel is an artist, illustrator, designer, and children’s book author who loves spending time hiking and doodling. Her most recent book, Priya Dreams of Marigolds and Masala, was published in 2019 and received a 2020 South Asia Book Award. Patel previously collaborated with Cloud9 Fabrics to create whimsical garden-inspired patterns that show how people are intertwined with nature. Here’s where she hangs out in the Bay Area.

Denver, Colorado

Keystone Resort

“I don’t want to sound cliché, but going to Denver brings out my inner cowboy,” says chef Ludo Lefebvre, founder of Chez Maggy restaurant in Denver’s Thompson Hotel. Originally based in Los Angeles, Lefebvre is new to the Mile High City, which has no shortage of places to stay, eat, drink, and explore. So we asked for his favorite spots in his new favorite town. Read the full guide here.

Steamboat Springs, Colorado

Frank Walter/Steamboat Springs Chamber

Based in Steamboat Springs, Hala Gear offers all the inflatable boards, paddles, and guidance you need to stand-up paddleboard with ease. Ahead of summer adventures on nearby lakes, we asked marketing director Victoria Ohegyi for her top spots to visit. Fun fact: She used to help prep breakfast at Mariposa Lodge Bed & Breakfast, and also worked at Off The Beaten Path shop where you’ll find a “stellar used book section.” Read the full guide here.

Maui, Hawaii

Anna Kim Photography

Walk into the Best Western Pioneer Inn, and you’re stepping into a piece of history; the hotel has been operating on Maui since 1901. “Every room boasts a second-floor outdoor lanai that overlooks either busy Front Street and one of the largest banyan trees in the country, or the peacefully hidden historic courtyard on the interior of the hotel,” says Lee Anne Wong, a previous Top Chef contestant and producer who’s now behind the onsite restaurant Papa ́aina. The menu features “locally sourced and inspired brunch fare,” Wong says, like macadamia nut ricotta pancakes and crispy ramen with kalua pork. Here are the chef’s must-visit stops in Lahaina and beyond.

Boise, Idaho

Courtesy of Push & Pour

Head east just beyond Boise, and you’ll find Roots Zero Waste Market in Garden City, a must-stop on any trip to Idaho’s capital. Bring your own jar to stock up on beans, vinegars, and spices. Léa Rainey and Zach Yunker opened the shop to help you “buy the amount you need when you need it,” as they say. Here are their favorite spots in the two cities.

Big Sky, Montana

Gallatin River Rafting. Photo courtesy of Field and Forest for Visit Big Sky.

The best time to visit this mountain town is after the Fourth of July, according to Christine Lugo-Yergensen. Late summer is replete with music in the mountains, farmers markets, and the like. Start your trip with breakfast at the chef’s patisserie Sweet Buns Catering, where you’ll find fruity pebble macarons. Then, head out to experience more top picks from the local chef and mom of three, who’s working on a book of high-elevation baking recipes. Read her full guide here.

Santa Fe, New Mexico

Courtesy of Heritage Hotels & Resorts

Chef Fernando Olea is a mainstay in the Santa Fe dining scene. He’s been serving up a highly curated menu of Mexican dishes since 1991, including a wide variety of specially made moles. On the heels of a 2022 James Beard award for Best Chef: Southwest, we asked Olea for his favorite spots to spend time in town. Read his full guide here.

Portland, Oregon

Gary Peterson

Baja California flavors meet Pacific Northwest bounty in Maylin Chavez’s seafood-centric cuisine. The Portland chef, who was born and raised in Tijuana, turned her oyster and wine bar Olympia Oyster Bar into a roving pop-up amid the pandemic, but her next brick-and-mortar is in the works. “Nothing is cookie-cutter here,” Chavez says. “That’s what makes Portland a really diverse and entertaining city.” Read her full guide here.

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