Outdoor markets, warmly lit downtowns, cozy restaurants, cheerful locals... there is something special about American…
There is so much talk about eating seasonally. Why not take that same approach to travel? Destinations simply shine certain times of the year. With that in mind, here’s a few destinations you should consider in October.
Hudson Valley – New York
Want a spectacular fall drive? Head to the Hudson Valley! It offers all of the criteria an autumn drive must meet: a Sinuous a la “car commercial” road, sweeping vistas, elevation changes, barns, barns, and more barns. Add in great food and drink, and you’ve got the perfect fall weekend.
Why go now? Pumpkin patches. Apple orchards. Beautiful winding roads with fall colors.
Where to stay: I adore the village of Millerton. It’s a charming hamlet with antique shops and art galleries. There are tons of B&Bs in town but stay at Troutbeck for something special. Surrounded by over 5,000 acres of countryside and forested areas, this upscale lodging in an 18th-century estate. Looking for something a little offbeat? Check out Wing’s Castle in Millbrook—a guest house and living art project 47+ years in the making! It looks like something out of Lord of the Rings, so if that speaks to you, get thee to this B&B.
Where to eat: Oakhurst Diner in Millerton offers a non-traditional diner menu. The last time I was there, they had a nice chicken Biryani for dinner. Curveball, right? Diner purists, don’t worry. They still have items like cheeseburgers, vanilla milkshakes, and deep-dish apple pie.
Multi-task! In October, Millbrook Vineyards & Winery holds family portrait days. Images can be turned into wine labels for Holiday gifts. Nothing says “this is why I drink” than a photo of your kids on a bottle of wine. And the wine is fantastic as well!
Farmer’s Market: A farmer’s market is a must-stop, and I love McEnroe Farm. A large sign out front marks what vegetables are fresh from their 1,000-acre family farm. Pour yourself a hot cup of coffee, grab an old-fashioned doughnut, and stock up on homemade jams and pickles.
Scenic Drive: It’s about the journey, not the destination. Look up “Salt Point NY” on Google Map. Now zoom out and find the main routes of 82 and 44. Use these two routes as your “bookends,” and all the roads in between become your playground. There’s not a bad one in the bunch. Some of my favorite roads to go down are Bangall-Amenia Road, County Road 83, and Carpenter Hill Road.
Read more about why I love Hudson Valley here.
There’s something intoxicating about Colorado (and no, I’m not talking about the legalized green stuff!). With a population of about 18,400, this old wild west town boasts great outdoor adventure, history, and culture. Here’s what to do in Durango.
Why go now: Fall colors and dazzling vistas. Best place to see it? On the Million Dollar Highway, a 70-mile strip of blacktop between Durango and Ouray. The road climbs up and over three separate passes: Coal Bank, Molas, and Red Mountain Pass. The breathtaking views make navigating all those hairpin turns, and sheer cliff drops worth the anxiety.
Where to stay: If you’re visiting a historic mining town, you might as well lean in. Book your stay at the Strater Hotel. This grand hotel dates back to 1887 and feels like it. Beautiful woodwork, stained glass, and masonry, plus a bona fide saloon that’ll have you expecting John Wayne to strut into the joint.
Where to eat: Durango is home to six craft breweries. Visit Steamworks Brewing Co. to sample local Kölsch, Imperial IPA, Steam Engine Lager, and more. Great sandwiches, pizza, burgers, and salads, too.
Where to shop: Historic Downtown Durango has it all— kids’ shops, clothing boutiques, art galleries, and vintage stores. The nationally acclaimed Toh-Atin Gallery showcases fine art from Native artists. Think jewelry, weavings, pottery, and vintage collection.
Not-so-stuffy-history lesson: Founded in the 1880s by the Denver & Rio Grande Railway, many vestigial reminders of its mining past exist. Learn about Durango’s seedier history of miners, madams, mayhem, and murders with Horsefly History tours. These intimate walking tours explore everything from the historic main streets to underground tunnels from the old mining days.
Ride the train: Want to experience Weminuche Wilderness as they did in the 1880s? Hop aboard the historic Denver & Rio Grande Railway. In addition to buying a train ticket, you can tack on adventure excursions, like zip-lining, white water rafting, horseback riding, ATV riding, and more.
Cultural significance: Durango puts you in close proximity to some of America’s most compelling first peoples, the Ancestral Pueblo. Spend a day at Mesa Verde National Park learning about the generations of people who built and lived in the cliffside cave dwellings. Want to get up close and personal? Take a ranger-guided tour. You must purchase tickets in person. Details here.
Read more about Durango here.
Orange County, California
Okay, OC. We get it. The weather is beautiful all the time. You can stop showing off now. That said, October is a lovely time to visit this part of California. It’s typically not oppressively hot but will likely feel like an extension of summer.
Why go now: Beaches. Sunshine. All the time.
Where to stay: Casa Laguna. The building dates back to the early 1900s and recently received a major facelift that enhanced its existing beauty. Of course, rooms this beautiful don’t come cheap. The goods news? If you’re just looking for a nice place to sleep, every hotel brand has a few outposts in the area. Find the one you’re racking up loyalty points for and book it.
Where to eat: Is there anything better than food-fired pizza and a nice bottle of red? Wine Gallery Laguna has you covered. Looking for a view? Check out Deck on Laguna, one of the only local restaurants on the sand. Expect fish tacos, burgers, and yummy salads.
Where to shop: Founded in 1993 by Shaheen and Linda Sadeghi (lovingly referred to as “The Last Hippies in the OC”), The LAB Anti-mall stands for “Little American Business,” and that’s exactly who you’ll find here. With shops, communal areas, yarn-bombed trees, live music, art installations, and food, the LAB isn’t about mass consumption—it’s about supporting and fostering creativity.
Get on the water: The Balboa Island Ferry started ferrying vehicles, cyclists, and pedestrians between Balboa Island and Balboa Peninsula in 1919. The family still operates the business, started by Joseph Allan Beek. Sure, this crossing in Newport Beach spans less than 900 feet, but it’s enough to really get into that relaxed, SoCal vibe.
Long walks on the beach: No trip to the OC is complete without a walk on the beach. Here, Main Beach gets all the press. It’s iconic—exactly what comes to mind when you think of a California beach. Love sea life? Keep an eye out for dolphins! You’ll find Heisler Park, home to many tide pools just to the north.
Small town charm: Spend a day bumming around Spanish-style San Clemente. Venture down the town’s Avenida Del Mar for shopping, dining, and the weekly farmers market. Be sure to make the 1296-foot-long walk out to the end of the San Clemente pier.
Read more about Orange County here.
When it comes to fall destinations, few can beat Salem, Massachusetts. That said, it’s not all witches and ghosts.
Why go now? Dubbed “Witch City,” there’s more history and supernatural speculation here than just about anywhere else in the country… perfect for Halloween lovers!
Where to stay: Check out The Merchant. The building dates back to 1784 and, in the years since, has served as a home, a tavern, an office building, and a rare book shop. Today, this historic, 11-room hotel mixes modern, fun, vibrant character with the building’s old-school charm. Spend the night in the same room George Washington did in 1789 (hint: it’s the room named after him).
Where to eat: Good bar food, cocktails, and classic arcade games? Count me in! Bit Bar offers next-level (video game puns!) mac and cheese, burgers, tater tots, and salads alongside your childhood favorite games. You really can’t go wrong with the food, so I guess the real question is which to play first: Centipede, Q-Bert, Miss Pac-Man, or Galaga.
Party with the locals: October is prime time to visit, with the Haunted Happenings celebration in full swing. There are parades, film nights, haunted houses, and more.
Weird fact: Cult classic Halloween flick, Hocus Pocus, takes place in Salem, and yes, it was filmed here.
Like spooky stuff? Book a ghost tour with Salem Historical Tours. This lantern-lit stroll features engaging guides that creatively convey Salem’s authentic haunted history.
Don’t like spooky stuff? Get out on the water with Mahi Harbor Cruises. You can opt for one of their specialty charter cruises from May to October. Think daytime trips with live music, sunset cocktail cruises, fall foliage, and lighthouse cruises.
Learn more about Salem here.
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