🍂 The Berkshires in the fall are everything you want in a cozy New England escape. In this guide, I’m sharing where to stay, what to do, and what to wear for the perfect autumn weekend—from charming inns and scenic drives to relaxed lunches, leaf-peeping, and cozy evenings by the fire. Think polished layers, rich fall tones, comfortable boots, classic knits, and effortless outfits made for crisp mornings and golden afternoons. Tap to shop the looks and plan your own chic Berkshires getaway. 🤎✨TheBerkshires FallTravel NewEnglandFall FallStyle TravelStyle AutumnOutfits WeekendGetaway CozyStyle LTKFinds LTKTravel LTKSeasonal LTKOver40 LTKTravel

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Leather-trimmed suede jacket | Mytheresa (US/CA)
Chocolate Aislinn Blouse | Tuckernuck (US)
Shon Corduroy Pants | Saks Fifth Avenue
Mija zebra-print calf hair belt | Mytheresa (US/CA)
Blackbird Shearling Mules | Shopbop
Canal Hoops - Gold | Mignonne Gavigan | Mignonne Gavigan
Monroe Crystal Strand Layered Necklace | Ettika
Black Polarized Majestic Sunglasses | Tuckernuck (US)
Kress Micro Crossbody | Leatherology