🍂 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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The Meg Plaid Top | Saks Fifth Avenue
The Ines Plaid Midi Skirt | Saks Fifth Avenue
Donna 80MM GG Canvas Slingback Pumps | Saks Fifth Avenue
Pardalis 2.0 Eel-Print Leather Shoulder Bag | Saks Fifth Avenue
The Lola Earrings | Shopbop
Whimsical Monet Mesh Party Top | Neiman Marcus
THE SHORTIE MISCHA SUPER HIGH RISE WIDE LEG | Favorite Daughter
Saige Heeled Booties | Shopbop
The Vancouver suede clutch | NET-A-PORTER (US)
Rue Cambon Earrings | Shopbop
Olivia Organza Skirt | Shopbop
Felicity Boxy Cropped Satin Button Down | Shopbop
Tiger's Eye Beaded Earrings | Tuckernuck (US)
Symmetry Pochette leather tote | NET-A-PORTER (US)
Gold Tassel Necklace | Tuckernuck (US)
Leather-trimmed suede jacket | Mytheresa (US/CA)
Midnight Navy Cashmere Sleeveless Ava Shell | Tuckernuck (US)
Sawyer Wide Leg Silk Pant - Prussian | Ulla Johnson
Calista Flat | Reformation (Global)
Chocolate Aislinn Blouse | Tuckernuck (US)
Shon Corduroy Pants | Saks Fifth Avenue
Mija zebra-print calf hair belt | Mytheresa (US/CA)
Laramie Removable-Collar Dickey Jacket | Shop.app
Mongolian Cashmere Tee | Quince
Palma Corduroy Straight Pants | Shopbop
Cashmere Zip Hoodie in Rich Burgundy | Quince
Mongolian Cashmere Sweatpants | Quince
Oat Shelby Rib Knit Tank | Tuckernuck (US)
Cyprus Boat Shoe In Brown Leather and Natural Shearling | Larroude
Charlotte Camera Bag - Olive | Ulla Johnson