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Chase Peak Fall Foliage: The Ultimate New England Autumn Road Trip Guide

Autumn transforms New England into a vibrant tapestry of color, with crisp mornings and sunny afternoons perfect for hiking, wine tasting, and apple picking. Leaf peepers and fall enthusiasts can follow this expert-curated road trip along the eastern seaboard, featuring handpicked hotels with harvest festivals, guided outdoor adventures, and farm-to-table dining.

Vermont
Peak foliage: Last week of September through mid-October

Pet-friendly Black Bear Lodge offers a free shuttle to Stratton Mountain's hiking trails, delivering 360-degree views across four mountain ranges. Rent bicycles, hike with your four-legged companions, or join the Columbus Day weekend harvest festival at Stratton Mountain Resort, complete with hay rides, pumpkin painting, live music, and craft beer tastings.

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Connecticut
Peak foliage: Late September through early November

Luxuriate at the Spa at Norwich Inn, ideally positioned along the 90-mile Connecticut Heritage Loop—a scenic drive from coastal vistas through Pachaug State Forest, Connecticut's largest. Unwind with seasonal body wraps, pedicures, complimentary afternoon tea and scones, wine tastings, guided nature walks, and outdoor meditation.

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Maine
Peak foliage: Mid- to late October

Locals rave about Maine's southern coastline in fall, when warm breezes meet abundant lobster. Across from pristine beaches, York Harbor Inn provides an exclusive hideaway amid private estates. Explore driving tours through nearby villages, state parks, and lakes, showcasing brilliant reds, purples, and golds framed by lighthouses and antique shops.

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Massachusetts
Peak foliage: Mid- to late October

From your private lakefront balcony at Black Swan Inn in the Berkshires—just 20 minutes from October Mountain State Forest, Massachusetts' largest woodland—embrace the season. Hike the Gorge Trail through crimson dogwoods and amber elms to Schermerhorn Gorge. On-site, rent kayaks, paddle boats, or pontoons to explore Laurel Lake. Nearby Tangier Outlets offers sweaters for cooler days.

Pennsylvania
Peak foliage: Early October into November

The Delaware Water Gap dazzles in autumn across 70,000 acres of rolling hills bursting with reds, oranges, and yellows. At the historic Shawnee Inn and Golf Resort on the riverbanks, enjoy kayaks, rafts, canoes, hiking trails, and golf. Evenings bring relaxation with ShawneeCraft Brewing Company beer—schedule a free tour and 6-ounce sample in advance.

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Travel Notes
  • Why Fall is the Perfect Time for an Epic Tennessee Road Trip

    Tennessees iconic destinations—Nashville, Memphis, Knoxville, Chattanooga, and the Great Smoky Mountains—each offer exceptional getaways. Link them into a single road trip, surround it with vibrant fall foliage, and layer in cant-miss events, and you create an unforgettable adventure.Even better: Tennessee is compact, so driving distances are short and manageable. Reaching the state is straightforward, with expanded direct flights to major airports like Memphis International, Nashville Internati

  • Polaroid of the Week: Stunning Fall Foliage in Upstate New York

    If youve read my October round-up, you know Im back in New York City! Returning last week brought a rare sense of calm and peace, allowing me to finally unpack. But before settling in, I embarked on a road trip to capture Upstate New Yorks fall foliage—the colors were fading fast, so I didnt hesitate.Last years quick trip to the Seven Lakes Drive was unforgettable, fueling my excitement for several days exploring the Hudson Valley, Peekskill area, and Catskill Mountains. I rented a car seamlessl

  • Polaroid of the Week: Breathtaking Leaf-Peeping Road Trip to Upstate New York s Bear Mountain

    I once thought I disliked fall, but Ive realized its November I dread, not the season itself. Last October and in 2011, I loved watching leaves transform in Chicago. This year in New York, the spectacle has been equally enchanting. Ive long dreamed of a Vermont fall getaway, renowned for North Americas most vibrant foliage from abundant maples bursting in orange and yellow. Though broader New England plans proved too ambitious, I carved out a day trip upstate. Convinced I could navigate NYC driv