What to Pack for Fall in the Berkshires: The Ultimate Guide

Fall in the Berkshires is one of New England’s most beautiful experiences. The rolling hills turn fiery shades of red, orange, and gold, local farms overflow with fresh apples and cider, and crisp mountain air makes hikes and scenic drives unforgettable. But if you’re planning a fall getaway, packing right is just as important as planning your itinerary. The weather here is unpredictable — chilly mornings in the 40s °F can quickly warm into sunny afternoons in the 60s or 70s. Add in the chance of rain or mist, and layers become your best friend.

Here’s the ultimate Berkshires fall packing guide to help you stay cozy, stylish, and prepared for anything.

Layering Is Key

The secret to enjoying fall in the Berkshires is dressing in layers. Start with base layers like long-sleeve shirts or thermals, add a cozy flannel or sweater, and top it with a light jacket or windbreaker. A packable rain jacket is a must — even if the forecast looks clear, New England weather can change quickly. This way, you can peel layers off during a sunny hike or bundle up for a chilly evening in Stockbridge or Lenox.

Footwear for Towns & Trails

The Berkshires is a place where you’ll want to explore — whether it’s hiking Monument Mountain, strolling through Great Barrington’s shops, or wandering the gardens at The Mount. Pack sturdy, comfortable shoes with good traction, like hiking boots or supportive sneakers. Waterproof options are ideal if you’re tackling damp trails or morning dew. For evenings, bring a pair of casual boots or nicer shoes for dining out.

Rain & Weather Protection

Fall weather here can shift in minutes. Be sure to bring:

• A compact umbrella or poncho for unexpected showers.

• Waterproof or water-resistant shoes.

• A rain shell or lightweight trench coat that doubles as a windbreaker.

This extra gear ensures a misty morning walk or surprise drizzle won’t ruin your plans.

Accessories & Extras

Little things go a long way toward making your Berkshires trip more comfortable:

• Warm add-ons: a hat, scarf, and gloves for sunrise hikes or nighttime events.

• Wool or thermal socks for extra coziness.

• Sunglasses and sunscreen — fall sun can still be strong, especially at higher elevations.

• Daypack to carry layers, snacks, and your camera.

• Lip balm and hand cream for the dry mountain air.

Optional: toss in hand warmers if you’re planning early morning foliage drives or spending evenings outdoors.

Final Thoughts

Packing for fall in the Berkshires is about balance: you want to be ready for brisk mornings, warm afternoons, and the possibility of rain — all in one day. With layers, good shoes, and a few smart extras, you’ll be prepared to enjoy every hike, harvest festival, and scenic drive the region has to offer.

Whether you’re road-tripping through Route 7, sipping cider at Hilltop Orchards, or catching a show at Shakespeare & Company, this packing guide ensures you’ll be comfortable enough to focus on the beauty around you.