15 Perfect Fall Trips To Take — Without Using Vacation Days

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Don’t be sad that summer is almost over. Instead, think about all the fabulous fall trips you can take once the seasons begin to change. An added bonus? It's usually a lot cheaper to travel in September and October than during the peak summer months.
Whether you’re looking for a traditional New England weekend getaway to see the autumn foliage, a city break, or a great beachside vacation, we’ve compiled 15 fall weekend trips you should consider. Just remember: Your Instagram followers can only handle so many photos of your journey without getting super jealous.
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Great Barrington, MA
Fall in New England is unparalleled, and the small town of Great Barrington, located in the Berkshires, is a good, non-touristy option. The town, which is home to a little over 7,000 people, has a beautiful array of fall foliage, best seen during a hike to Monument Mountain. There are tons of cute local restaurants, including the Barrington Brewery and Restaurant and Prairie Whale, and an amazing weekly farmer’s market that runs through the end of October. If you’re into vintage shopping, be sure to stop by Griffin for a carefully curated collection of clothes and classic items.
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Where To Stay:
The iconic Red Lion Inn is located in Stockbridge, about five minutes' drive from Great Barrington. You’ll love the absurdly kitschy vibe of the main inn building (which was built in 1773), but if that's too rustic, there are also several guest houses on the property that are slightly newer, with more modern amenities. There’s also a pool and hot tub, library, fitness center, and, famously, a lobby cat named Simon.
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Big Sur, CA
Rent a car in Los Angeles or San Francisco and drive the California coast to Big Sur, a coastal area that is perfect for the cooling months of fall. There are several beaches to visit, including the popular Julia Pfeiffer Burns State Park, and you’ll want to pack your hiking boots for a trek through Limekiln State Park. The Henry Miller Memorial Library is worth a visit, as is the Big Sur Deli, where you can grab a sandwich on your way to explore. For dinner, grab a table at the historic Nepenthe, which offers amazing views while you eat.
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Photo: Courtesy Of The Ventana Inn.
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Where To Stay:
For a truly unparalleled stay, head to the Ventana Big Sur, which looks out over the ocean from the mountains. The property has two heated outdoor pools (one of which is clothing-optional), Japanese baths, daily yoga classes, and afternoon wine receptions, so you’ll leave refreshed and infused with the magical energy of this place. The extraordinarily private rooms and suites are chic, spacious, and equipped with amenities such as private outdoor hot tubs and working fireplaces. Even if you can't afford a room (they're not cheap), swing by for lunch at the restaurant while you're in the area.
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Bucks County, PA
If you want to really experience fall in all its colorful, leafy glory, Bucks County is an ideal destination. The region, located only a short drive from Philadelphia (or a slightly longer drive from New York City), has Instagram-ready scenery, which you can view by biking along the Delaware River or hiking through Washington Crossing Park. Grab a meal at Bowman’s Tavern in New Hope or stop in at Southampton’s Steam Pub, and in the evening order a cocktail — or two — at speakeasy-style bar The Still.
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Where To Stay:
Hotel du Village is a really cool option. The hotel is generally used as an events venue for weddings, but if there are free rooms, you can snag one (as well as access to the pool and tennis courts). If it’s full, check out The Logan Inn, a small, historic hotel with a solid cocktail selection.
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Miami Beach, FL
It may be fall, but that doesn’t mean you can’t suck up a few more days of beachside sunshine in Miami Beach. Spend your weekend lying by the pool and on the sand, as well as exploring the city’s neighborhoods, like Little Havana, where you can snag a Cuban sandwich. Miami Beach has become well-known for its street art, so download a self-guided tour of some of the best murals and head out on one of the hippest walks of your life. The city also has incredible nightlife, and you’ll want to grab a drink at The Regent Cocktail Club or The Broken Shaker before hitting one of the many dance clubs.
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Where To Stay: Circa 39 is a cool boutique property located across the street from the beach. You can hang out by the pool, lounge in the courtyard garden, and drink at the hotel’s own WunderBar, which serves delicious rum-based cocktails perfect for the Florida heat.
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Burlington, VT
Burlington is a cool lakeside city that is laid-back and artsy. Lots of travelers head there in the autumn to see the leaves turn, and the best views are from the Burlington Bike Path. If you’re into beer, you can pay a visit to the Magic Hat Brewing Company, where you can tour the factory and indulge in a free tasting. For dinner, book a table at farm-to-table eatery Hen of the Wood or The Farmhouse Tap & Grill. Burlington is also home to several pumpkin patches and corn mazes, if you really want to get into the fall spirit.
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Where To Stay: Your best bet is Made INN Vermont, a trendy B&B that is as fun as its name. The hotel, which refers to itself as a “mini resort,” has great amenities, record players, tons of shared common spaces to hang out in and, of course, a hot tub.
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Asheville, NC
Located in the Blue Ridge Mountains, Asheville has become famous for its colorful fall leaves, which are at their best during October and early November. After you leisurely drive through the mountains to see the foliage, you can visit an apple orchard or Asheville Art In the Park, a local art festival that runs for three weekends in October. The Biltmore Estate, George Vanderbilt's historic country home, is worth a trip — despite its high price tag. And, the city offers several brewery tours. For evening cocktails, head to Sovereign Remedies, an off-the-beaten-path joint with great drinks.
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Where To Stay: The best spot for your fall trip to Asheville is the Grand Bohemian Hotel, a cool property that mixes rustic design elements with modern comfort and luxury. The lobby is legitimately impressive, but if you can break away from the hotel, most of the town's shops and restaurants are only a short walk away.
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Boston, MA
Attention baseball fans: The Red Sox continue their season through September, so you can take in a game at the historic Fenway Park during your stay in Boston. Explore the Freedom Trail through the city and visit the Museum of Fine Arts before shopping along Newbury Street. The Union Oyster House is a must-visit to experience local seafood, and Sarma, a Middle Eastern restaurant off the beaten path, is memorable. If you like music, the city is filled with amazing venues, including TT The Bear’s Place and The Middle East.
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Where To Stay: Try boutique hotel The Verb, situated directly adjacent to Fenway Park. The low-key hotel has a colorful, vintage vibe with an outdoor pool, fitness center, and lots of nearby shops and bars.
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Cotswolds, U.K.
London’s chicest inhabitants head to the Cotswolds in the summer and fall, only a short train ride away from the city. The countryside region has several small towns to explore, including celebrity favorite Chipping Norton and quaint Hook Norton. Your best bet is to rent a car so you can drive through the rolling green hills and visit the nearby Blenheim Palace and Gloucester Cathedral. Really, though, you should post up at a local pub, order a Sunday roast, and imbibe several pints of beers — just like a real Brit.
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Where To Stay: Soho Farmhouse, an offshoot of Soho House, is located in Chipping Norton and rents out its chic cabins even if you aren’t a member of the club. There, you can eat, drink, go to the spa, horseback-ride, and indulge in the property’s indoor/outdoor boathouse swimming pool.
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Munich, Germany
If you’ve always dreamed of attending a real German Oktoberfest, book a flight to Munich. The city’s annual festival runs from September 17 until October 3 and features rides and fair attractions, vendors, and lots and lots of beer. There is, of course, far more to see in the city than just the bottom of a pint glass. The BMW Museum is a favorite for car enthusiasts, and the Nyphenburg Palace and its surrounding gardens are worth checking out. The recently opened Museum Brandhorst is home to a vast selection of modern and contemporary art, and the Jewish Museum offers a history of Jewish culture and faith.
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Where To Stay: Grab a room at the centrally located Anna Hotel, a modern, well-appointed boutique hotel. The property allows guests to use the “wellness oasis” in the adjacent Hotel Königshof Munich, so you’ll be sure to have a respite from the city and its many, many beers.
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Kennebunkport, ME
Kennebunkport bills itself as “The Place To Be All Year,” but you’ll especially appreciate the small Maine town in the autumn. The cute town, located along the water, is full of art galleries, restaurants, and ocean activities like kayaking, whale watching, and surfing. Grab a latte at Dock Square Coffee House and stroll through downtown to visit the many local shops. In the evening, Old Vines Wine Bar is a good spot to grab a glass of vino, and you can enjoy a farm-to-table meal at Earth, a restaurant on the grounds of the Hidden Pond Resort.
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Where To Stay: Hit up traditional, quaint bed-and-breakfast 1802 House, which offers six guest rooms, three-course gourmet breakfasts, and the sort of personal service you can only find at small, charming inns in the Northeast. The hotel can also help you book a bike, so you can cycle through the changing trees.
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Charleston, SC
Charleston was recently dubbed the “Best City In the World” by Travel + Leisure, so you should pay a visit to the Southern locale to see for yourself. The city, founded back in 1670, still has cobblestone streets and old, classic buildings. Its long history is on display in the architecture and tourist sites, which include Fort Sumpter, and it is well known for its local food and music. Be sure to throw back some oysters at Pearlz Oyster Bar and pull up a chair at Hominy Grill, which serves up local favorites like the Charleston Nasty Biscuit (which features fried chicken breast, cheddar cheese and sausage gravy).
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Photo: Courtesy of The Vendue.
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Where To Stay: The Vendue, which is dubbed “Charleston’s Art Hotel,” is a must-stay while in the Southern city. It has its own art collection, eclectic, luxe rooms and complimentary bike rentals to help you explore the town.
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Havana, Cuba
Havana has become a popular destination thanks to several U.S. airlines now offering flights to the Cuban city (including JetBlue, which recently announced its routes). Explore Old Havana, visit the National Museum of Fine Arts and saunter down The Malecón, a seaside boulevard that extends through the city. If you care about cigars, you can try to book a visit to the Partagas factory (which only sometimes allows visitors), and be sure to grab a table at La Casa de la Música for live music and dancing. And, obviously, you’ll need to order a daiquiri at Floridita, which is famous for hosting Ernest Hemingway during his time in Havana.
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Where To Stay: Havana has a burgeoning Airbnb scene that is worth looking into, but if you want a traditional hotel check out the Saratoga, one of the city’s iconic hotels. There you’ll find well-appointed rooms, three bars and a pool.
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Anchorage, AK
Anchorage is the perfect gateway to a slew of outdoor Alaskan activities like fishing, hiking, glacier trips and wildlife viewing. Spend at least one day out in the wilderness (the Tony Knowles Coastal Train is a popular hiking path) and then devote some time to the city itself, which has an interesting museum called the Alaskan Native Heritage Center. The city has a fairly low-key culinary scene, so pull up a stool at Moose Tooth Pub and Pizzeria for a local vibe. Later, for a drink, try the Glacier Brewhouse or dive bar Darwin’s Theory.
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Where To Stay: Anchorage mainly has big chain hotels, but if you want something with more of a local spark try the Copper Whale Inn, a small B&B located near downtown. It’s got a rustic aesthetic, but the breakfast is plentiful and free, and fall room rates are a serious bargain.
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Vieques, Puerto Rico
We get it: You don’t want to let summer slip away. And technically, you don’t have to. Isla de Vieques, an island that is part of Puerto Rico, is a lesser-known island destination that will give you all the sunshine and sand you need. You can snorkel, kayak, lay on the beach or go stand-up paddleboarding at several ocean spots. A nighttime trip to Bioluminescent Bay is a must-do, where you can experience the naturally glowing water. Eat some local cuisine at Coqui Fire Café or Tin Box, and don’t forget to stop by the funky Sol Food for lunch one day.
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Where To Stay: You can either splurge and book a room at the chic W Retreat & Spa or go with a more low-key beach feel at Hacienda Tamarindo, both of which look over the ocean. The latter offers the much-beloved honor bar, which allows guests to imbibe any time of night (or day).
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Montreal, Canada
Montreal is a quick flight from the East Coast, but feels like a faraway European destination. The Canadian city, a charming place to spend a weekend, has art museums, history and tons of cafes where you can sit and drink coffee all afternoon. Be sure to grab a truly iconic bagel from St-Viateur Bagel and visit a location of Frite Alors for poutine, a classic dish that involves French fries covered in gravy and cheese curds. The city has an intense amount of bars, so it won’t be hard to land somewhere great in the evenings (but if you need a tip look for speakeasy Bar Cloakroom).
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Where To Stay: Montreal has tons of amazing (and often pricey) hotels. But Petit Hotel Montreal, located in the center of downtown, is a cute, contemporary option with its own — equally cute — café.
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