The Underrated US City You Need To Visit For Your Next Long Weekend
Idyllic escapes that don’t require a passport.
If spring symbolizes rebirth, fall is surely the season of recharging — a time for slowing down and savoring life’s simplest pleasures. Naturally, autumn serves as the perfect backdrop for a weekend getaway and if you’ve been itching for an adventure but don’t have the bandwidth to take off time from work or family, why not consider an easy-to-reach destination? There are, of course, the staple visits like Los Angeles, New York, Miami, and so on. But if you want to head somewhere that feels a pinch out of the ordinary, you won’t fall short of options. Below, discover a roundup of 15 magical US cities for a quick fall getaway.
These wondrous places are scattered throughout America and each offer a unique perspective. Whether it’s somewhere that leans into its past with preserved architecture and historic landmarks, or regions that relish in their natural surroundings like creekside cottages and mountainous boutique hotels — there’s something for every kind of traveler.
Yes, Europe is nice and a luxe vacation abroad is the stuff of dreams but so, too, can a quick jaunt be to a picturesque town in your own backyard (or country). Not sure where to start? Ahead, find your next great escape and add a few itinerary items to your journey along the way.
Great Barrington, Massachusetts
The Berkshires, situated in western Massachusetts, are a cluster of villages that ooze with small-town charm (think farm-to-table dining, literary and musical history, independently owned shops, autumn leaves as far as the eyes can see — the works). One of those towns, Great Barrington, is a fine hub for your weekend getaway. Book one of the eight themed suites at The Barrington located on Main Street or, if you prefer more casual digs, a room at Briarcliff Motel is also a good choice (it’s a ‘60s-era-motel-turned-contemporary-motor-lodge).
Indulge in the extensive assortment of artisanal cheeses at Rubiner’s Cheesemongers & Grocers started by Matthew Rubiner. His other project, Rubi’s Cafe, is a coffee and sandwich shop that’s worth a visit (tip: order the grilled cheese). If you arrived by car, be sure to drive around the surrounding towns for a more immersive Berkshires experience. Stop highlights might include MASS MoCA in North Adams, The Mount (Edith Wharton’s turn-of-the-century home) in Lenox, and the Berkshire Botanical Garden in Stockbridge. Or, stay in Great Barrington and hike up Monument Mountain to take in the natural splendor.
Park City, Utah
With a towering elevation of 7,000 feet, many travelers associate Park City with ski culture. But it’s a destination that also thrives in autumn thanks to Utah’s atmospheric changing colors and an outdoor scene that offers off-the-grid adventures like fly fishing, horseback riding, hiking, and mountain biking. You’ll want to book your stay at The Lodge at Blue Sky, which is part of the Auberge Resorts Collection. The freestanding Creek Houses are one-bedroom suites that dot the babbling banks of Alexander Creek. There’s also the Washington School House, a boutique hotel originally built as a school in 1889 that features 12 rooms within its historic limestone walls.
If you make it here earlier in the season, the Park City Wine Fest is a festive itinerary activity. If your dates don’t align, there’s also the nearby High West Distillery & Tasting Room where visitors can book a Sensory Tour Experience. After a stroll along the historic Main Street and stopping at the Farmers Market (every Wednesday 12 p.m. to 6 p.m. through October 19), hop on a bike to explore the Historic Pacific Union Rail Trail. You can also see the city from a bird’s eye view with one of the region’s hot air balloon pilots. Over at The Lodge at Blue Sky, you can partake in the resort’s Heli Adventures; a series of activities like fishing, skiing, yoga, and hiking — all accessed via helicopter. And last but not least, scenic drives are a must during this time of year, and they’re all within a few miles of Park City.
Highlands, North Carolina
Within the Nantahala National Forest in the southern Appalachian Mountains lies the quaint town of Highlands. It’s the place to go if your idea of the perfect getaway involves staying in a charming mountain hotel and spending your days dining and taking in nature. Check in at Highlander Mountain House — a boutique hotel that nods to an Appalachian-lodge-meets-English-country-estate. There are roaring fireplaces, Josef Albers paintings, and an onsite tavern that serves up seasonal dishes and wine from family run vineyards in an old-world setting.
During your time here, forest bathe on one of the many surrounding nature trails and waterfalls. Afterwards, unwind at one of the town’s standout dining destinations, like Wolfgang’s and Madison’s located in Old Edwards Inn & Spa. And for those seeking art and culture, Highlands has The Bascom — a visual arts center — and Highlands Playhouse — a performing arts theater that's been around since 1939.
Door County, Wisconsin
Located on a peninsula in the ‘left thumb’ of Wisconsin sandwiched between Lake Michigan and Green Bay, Door County is renowned for its breathtaking scenery, best explored by its coastal byway and within its extensive park system. It’s made up of over 2,000 square miles and 19 communities, so if you choose to visit this magical region, you’ll need a car. Accommodations run the gamut in Door County, ranging from campgrounds and B&Bs to hotels and log cabins. White Gull Inn in Fishcreek is an intimate bed and breakfast that opened its doors in 1896 and is open all year round.
While exploring the county, you’ll encounter architecture that’s reminiscent of early Native American residents as well as Scandinavian and Belgian settlers (tip: go see The Stavkirke — a Norweigian-inspired medieval stave church in the Washington Island woods). Other autumnal activities in Door County include farmers markets, fishing trips, birding excursions, and tours of the region’s 11 lighthouses, which were constructed in the 1800s. Oh, and shipwrecks. There are, at present, around 240 known shipwrecks in the waters that surround Door County and visitors can catch glimpses of 25 of them through shipwreck diving, clear-bottom kayak tours, boat rides, and maritime museums.
Colorado is a playground for adventure, and destinations like Denver, Boulder, Aspen, Telluride, and Breckenridge are all likely on your radar. If you’re interested in visiting a lesser-known town in The Centennial State, head a few hours south of Denver to Salida. With a tiny population and a high concentration of fourteeners (14,000-feet-and-above mountains), it’s no surprise this small spot lives up to its undiscovered aesthetic. Amigo Motor Lodge designed its guest rooms and airstreams in the spirit of “Southwestern flair” and there’s a hot tub for soaking and a sunroom for relaxing.
Howl Mercantile and Coffee is a charming spot in town to grab a latte and shop a curated assortment of goods like homewares, jewelry, and adventure equipment. Of course, you come to a place like Salida for the surrounding nature so be sure to get in a few hikes while you're in town (Old Monarch Pass Loop and Shirley Site Trail are both good places to start). Once you’ve gotten back and showered, head for Soulcraft Brewing for a refreshing beer (and maybe some buffalo chicken wings, too).
Hood River, Oregon
One hour outside Portland is one of Oregon’s most breathtaking regions: the Columbia River Gorge. Located in this region is Hood River, a (yet again) charming town that has just about everything you could ever want out of a weekend getaway: otherworldly outdoor activities, world class food and beverage experiences, and an overall sense of slowing down. The Columbia River divides Washington and Oregon and the hotel you should book is technically in Bingen, Washington (a 10-minute drive from Hood River proper). The Society Hotel is a converted schoolhouse from the ’30s originally designed by Pacific Northwest architect Donald J. Stewart.
Among the more distinct experiences in this area is the Fruit Loop — a scenic 35-mile loop in the Hood River Valley dotted with farm stands, wineries, and lavender farms where you can pick your own fruit, enjoy a wine or cider tasting, and take in the crisp autumn air. As for nature, you’ll be spoilt for choice when it comes to choosing a hike (Latourell Falls Loop and Hamilton Mountain are both great places to start).
Wine-lovers should book their fall getaway in Healdsburg, a small-town within Sonoma County that’s located 45 miles north of San Francisco and along the Russian River. Wine is the star attraction in this region but that doesn’t mean there aren’t myriad activities to balance out your stay (more on that in a moment). Finding the perfect hotel here isn’t an issue — it’s choosing between them. River Belle Inn is a boutique luxury property that’s situated on the banks of the river and serves a locally sourced and organic breakfast. The Madrona, designed by Jay Jeffers, opened earlier this year and is worth a bookmark as well. And if you’re an eco-traveler, h2hotel with its succulent-bedecked roof and LEED certification is another favorite.
Horseback riding, hot air balloon rides, canoe and kayak trips, antique shopping, art classes — Healdsburg activities aren’t messing around. And when you do finally get around to wine tasting, don’t miss out on nearby Medlock Ames, Aperture Cellars, and Flowers (among many others).
Leaf peepers flock to Vermont come fall and though Stowe is a popular destination among travelers, two-and-a-half hours south in Manchester, another autumnal delight awaits. Nestled in the ‘Green Mountains’, this small town is where New England charm hits its stride with locally owned shops, charming hotels and inns, and plenty of opportunities to take in the scenery. Treat yourself to a stay at The Equinox Golf Resort & Spa, which offers seasonal activities like guided hiking, axe-throwing, Orvis-lead fly fishing and clay shooting, falconry, and Land Rover off-roading driving school.
In town, enjoy blood-pressure-reducing outings like the Seven Springs Garden & Sculpture Park, which offers visitors 20 acres of gardens, fields, and orchards and two miles worth of winding footpaths. There’s also the local farmers market that’s open from the end of May until early October. And as for food, don’t leave without having a meal at The Chantecleer. It's set inside a remodeled dairy barn and the menu has a “seafood focus and a French touch.” It’s also got a horseshoe-shaped bar.
If you live for an immersive travel experience, head to Leavenworth in Washington. In the 1960s, town leaders decided to give Leavenworth a facelift and completely renovated it to resemble a Bavarian style village to match its surrounding alpine hills. Book a room at Posthotel as your home base; it’s an adults-only spa resort that has amenities like a saltwater swim-out pool and spa and European hydrotherapy traditions.
In the fall, visitors can partake in mountain biking, zip lining, hiking, and horseback riding. Or, if you’re leaning toward a more relaxed day, try something like a wagon and carriage ride through town. You can expect authentic German cuisine while here so gear up for brats and beer (and schnitzel, too).
Chimayó, New Mexico
You’ve heard of Santa Fe. Taos, too. But what about Chimayó? If you’re seeking an off-the-beaten-path experience in New Mexico, this small village is worth a visit. It’s located in the foothills of the Sangre de Cristo Mountains and is best known for its historic church called El Santuario de Chimayó. The Casita at Casa Escondida Bed & Breakfast is a one-bedroom adobe suite featuring design touches like Saltillo tile floors and an indoor fireplace.
The side chapel at the church has a dirt floor that is said to have healing powers and every Good Fridays, tens of thousands of journey to this small sanctuary. Chimayó is also regarded for its weaving community, so you should visit Centinela Traditional Weaving Arts and Ortega’s Weaving. Once you’ve worked up an appetite, Rancho de Chimayó will be there waiting with its menu of delicious New Mexico cuisine (think spicy guacamole, hand-rolled tamales, and blue corn enchiladas).
St. Augustine, Florida
St. Augustine is the oldest city in the United States and is beloved for its Spanish colonial architecture. Historic avenues and cobblestoned corridors lead to magnificent bridges and gates, giving any visit to this place an immersive historical feel. Start your journey by checking in at Casa Monica, a hotel that dates back to 1888 and delivers a blend of Moorish Revival and Spanish Baroque architectural styles.
Next, take a stroll along historic Saint George and Aviles Street to experience quaint shops, galleries, and eateries. A 10-minute walk from there will take you to the Old City Gates, which features coquina blocks dating back to 1808. If you’ve come for the Gilded Age architecture, Lightner Museum, Flagler Memorial Presbyterian Church, Cathedral Basilica, and Villa Zorayda Museum should all be on your list. St. Augustine also offers a slew of tasty tapas restaurants, including Columbia Restaurant, which has been around since 1905. Michael’s is another solid choice thanks to its location on the scenic Calle Cuna. Its menu changes seasonally with a focus on steaks and Spanish-inspired cuisine. Snag a seat in the backyard for an especially magical meal.
Deadwood, South Dakota
Towns that harken back to gold rush era are an out-of-the-box treat, which is why Deadwood in the southern Black Hills of South Dakota should be on your bucket list (fun fact: the entire town is a National Historic Landmark). Brimming with history, Deadwood is so dedicated to its vibe that there’s even a theater troupe that walks around town and reenacts major historic events like the trial of Jack McCall and Wild Bill’s assassination. Stay at the Martin Mason Hotel, a restored Victorian hotel from the 1890s that’s furnished entirely with antique and period decor.
Wild West re-enactments aside, there’s tons of things to do in this area ranging from nearby Mount Rushmore (one hour away) to the Broken Boot Gold Mine where you can step into an underground mine for a candlelight tour. There are casinos and wineries and breweries for a dose of debauchery and even a few ghost tours for some spooky fun. For a family friendly outing, hop onboard the 1880 Train, a two-hour, narrated 20-mile round trip between Hill City and Keystone. It’s basically adult Disneyland and there’s no reason not to make it your fall getaway.
Savannah is one of those US cities that, despite its popularity, manages to maintain its distinctive charm. With its Spanish moss and atmospheric architecture, a visit feels all but necessary during this time of year. There are countless options for accommodations in this special city — why not go for newness and book a room at the recently opened Thompson? It’s located along the Savannah River’s edge and has a rooftop bar for those who like their cocktail with a side of panoramic views.
You’ll learn quickly that this city takes its ghost tours very seriously, so if a spooky stroll sounds appealing, you’ll have plenty to choose from. Spirits aside, a regular stroll in the Victorian District and in Forsyth Park is an itinerary highlight, as is the Historic District. Afterward, grab a bite at The Grey, a restaurant located inside a 1938 art deco Greyhound Bus Terminal and at the helm of Chef Mashama Bailey.
Hudson, New York
There’s a reason why everyone loves upstate New York — it’s ineffable. And while this area is picturesque year round, there’s something about fall in a place like Hudson that feels especially fitting. This historic town used to be a whaling port in the 1700s but now it’s the epitome of a small town with its antique shops, quaint coffee shops and stores, and unique accommodations. One of these is This Old Hudson, a turn-of-the-century home that’s been renovated by Zio and Sons. It’s furnished with vintage objects and artful details like a cast iron tub and brass fixtures and has all the amenities for a low-key weekend getaway (e.g., washer and dryer in unit, full kitchen, and private porch for evening meals and sips).
Start your day with brunch at The Maker Hotel's cafe, it feels like an Old World European lounge and is the perfect place to slow down and read a book. Next, head for The Antique Warehouse where you could easily spend a day unearthing treasures for your home. Afterwards, a few steps away, enjoy a pint of beer and game of darts at Hudson Brewing Company and follow that up with dinner at Hudson Food Studio, which serves up exquisite southeast asian inspired cuisine.
Harpers Ferry, West Virginia
Last up is Harpers Ferry, truly one of the most autumnal places you’ll ever encounter. It’s a historic town that’s where the Potomac and Shenandoah rivers meet as well as where the US states of Maryland, Virginia, and West Virginia meet. It played a huge part in the Civil War and was the site of abolitionist John Brown’s raid. Book a room at The Jackson Rose Bed and Breakfast and sleep inside a restored Federal-style home with pine floors and gas fireplaces (plus a front porch overlooking rose and herb gardens).
History and nature will be your two main themes during a weekend away in Harpers Ferry. Explore the Lower Town historic area followed up by a hike on the Maryland Heights Trail for magnificent scenery (it takes around three to four hours to complete). Afterwards, recharge at H.B. Snallygaster’s General Store & Cafe.
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