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Key Points Fall getaways are matched to personality types like homebody, adventurer, or culture seeker. Recommendations include Hudson, Bozeman, Milwaukee, Greenville, and Carmel-by-the-Sea. Each destination offers tailored activities, lodging, and dining for distinct traveler preferences. Fall is the perfect time to travel—the air is crisp, the crowds are fewer and the landscapes shimmer in reds, greens and golds. But not everyone wants the same kind of escape. Some are all about the charm of a small town—Gilmore Girls style, others love a good fall road trip, while some are happiest catching a show and trying a new restaurants in an up-and-coming city. Your personality type can actually reveal a lot about what kind of fall getaway will truly recharge you. Whether you’re a planner, a wanderer or somewhere in between, here’s the autumn escape that’s perfect for you. Related: 7 Fall Foliage Destinations Everyone Should Visit Once, According to Darley Newman For the Cozy Homebody If your ideal weekend involves a good book, a soft sweater and a delicious latte, Hudson, NY, is your perfect fall escape. The stylish, walkable town has quietly become a hub for design lovers and cozy travelers alike. Stroll down Warren Street, where nearly every block is filled with antique shops, indie bookstores and out-of-the-way cafés. For an ultra-cozy stay, check into The Maker Hotel, a chic property that exudes vintage glamour with fireplaces and velvet sofas, or the Rivertown Lodge, a minimalist inn housed in a former movie theater. Start your morning with a warm croissant and espresso at Breadfolks, browse the treasures at Finch Hudson or Red Chair on Warren, then grab dinner at farm-to-table outpost Wm. Farmer and Sons, known for its seasonal menu and intimate bar. Related: 7 Biggest Fall Travel Trends of 2025, According to Travel Pros For the Adventurous Explorer For travelers who love early mornings on the trail and stunning natural backdrops, Bozeman, Montana, has that rare mix of rugged adventure and a quietly sophisticated local scene. Base yourself at the Kimpton Armory Hotel, a restored Art Deco luxury find with a rooftop pool overlooking the peaks, or the RSVP Motel, a retro-chic boutique hotel with a killer “field-to-table” café. Spend your mornings exploring nearby Hyalite Canyon, a local favorite for fall hikes past golden aspens, or opt for a scenic day trip to Yellowstone National Park, less than 90 minutes away. Back in town, grab a coffee and pastry at Treeline Coffee Roasters, shop for outdoor gear and home goods at Heyday or Montana Supply, and cap off the night with cocktails and dinner at Blackbird, an always-buzzy wood-fired Italian spot in the center of town. Related: The Cozy Canadian Cruise That’s a Hidden Gem for Fall Views For the Culture Seeker If you find yourself drawn to the latest gallery exhibitions or people-watching over coffee, Milwaukee, Wisconsin, blends Midwestern warmth with serious cultural cred. The Milwaukee Art Museum—with its iconic Santiago Calatrava–designed “wings”—is a must-visit, especially in fall when the lake is lined with colorful foliage. Stay at The Pfister Hotel, a Gilded Age landmark with stunning architecture, or The Journeyman, a stylish boutique stay in the trending Historic Third Ward loft district. Mornings can be spent strolling the RiverWalk and grabbing a latte at local spot Colectivo Coffee, followed by gallery hopping and browsing indie boutiques like MOD GEN and Third Coast Style. For dinner, Ardent delivers a Michelin-worthy tasting menu, or you can go casual with Harbor House, a waterfront spot for oysters and wine. For the Social Butterfly If your ideal trip includes live music, bustling restaurants and meeting new people, Greenville, South Carolina, hits the sweet spot between lively and laid-back. One of the most charming small cities in the South, it’s perfect for travelers who love the latest up-and-coming restaurants and walkable dowtowns. Stay at the Grand Bohemian Lodge, a luxe, wood-and-stone retreat right on the river, or check into Aloft Greenville Downtown for a more modern, social vibe. Start your day with a walk across Falls Park on the Reedy, where a waterfall cuts through downtown, then grab coffee and a flaky biscuit at Methodical Coffee. Later, explore the boutiques along Main Street—Mast General Store and Savereign are favorites—before grabbing cocktails at rooftop-bar Juniper. Cap off the night with dinner at Jianna, a lively Italian spot with fresh pasta and a killer Aperol spritz. For the Romantic Dreamer
