09/16/2026
Plan some R&R in the Berkshires this fall! Stay 3 consecutive nights Sunday through Thursday and get 25% of your entire reservation! Use promo code 25% WEEKDAY DISCOUNT or call us at 413-447-9419 and our super helpful, friendly, cheerful and professional staff will make a reservation for you! Fall is beautiful here! Come stay with us!
🍁 STEAL THIS PERFECT 1-DAY BERKSHIRES FALL ITINERARY! 🍂🚗
If you’re dreaming of quaint New England towns, mountain views, historic estates and incredible fall foliage, save this road trip through The Berkshires, Massachusetts. It packs some of the region’s best stops into one beautiful fall day without trying to do everything. ❤️
📍 SAVE THIS ROUTE:
🍂 8:30 AM: Stockbridge
Start on historic Main Street, grab coffee, browse the shops and see the iconic Red Lion Inn. This little town is basically New England fall in real life.
📚 10:15 AM: The Mount, Lenox
Explore the beautiful home and gardens of Pulitzer Prize-winning author Edith Wharton. Even the drive and grounds are worth adding to your Berkshires itinerary.
🍽️ 12:00 PM: Downtown Lenox
Stop for lunch, then wander the local shops, galleries and charming downtown streets.
🏔️ 1:15 PM: Olivia’s Overlook
One of the easiest ways to get a BIG Berkshire view without a long hike. During peak foliage, the rolling hills become a sea of red, orange and gold. 😍
🍁 2:30 PM: Mount Greylock
Finish with the grand finale: Mount Greylock, the highest point in Massachusetts at 3,491 feet. When the seasonal summit road is open, drive to the top for sweeping views and the Veterans War Memorial Tower.
🎃 BONUS: Naumkeag
Visiting during its open season? Naumkeag in Stockbridge is a gorgeous Gilded Age estate and garden worth considering. In October, the ticketed Incredible Naumkeag Pumpkin Show makes it an especially fun seasonal addition. Check current dates and tickets before building it into your day.
⚠️ FALL TRAVEL TIP: Mount Greylock’s summit road is seasonal and weather-dependent, and attraction hours can change. Always check conditions before heading out - especially late in the fall.
✨ BEST TIME FOR THIS ROAD TRIP: Generally late September through mid-October for fall color, although peak foliage varies every year.
This is the kind of fall day we LOVE: small towns, historic homes, local food, scenic roads and one incredible view after another. 🍁
📌 SAVE this Berkshires itinerary for your fall New England road trip and SHARE it with the person you’d spend a crisp autumn day exploring with!
Would you rather spend your fall day exploring the small towns 🍂 or chasing mountain views 🏔️?