The Berkshires.
Quietly devastating in October.
Western Massachusetts at its best — Tanglewood concerts in summer, fall foliage that genuinely stops traffic, MASS MoCA in winter, and a chain of inns and farm-to-table restaurants that's been a New England weekend staple for a century. About 2.5 hours from our Stamford home pickup.
Mass Pike. Foliage. A quiet cabin.
The drive from Stamford to the Berkshires is one of the most rewarding road trips in the Northeast — straight up the Taconic or out through the Mass Pike, both options stretching out into rolling hills that get progressively prettier the further west you go. In peak fall (mid-October), the colors are genuinely the kind people fly across the world to see.
The Tesla shines on this trip for one specific reason: the cabin is the quietest place in the Berkshires to talk to whoever you brought. No engine droning over your conversation, no gas-station math at the Mass Pike rest stops. Plug in at Tanglewood's destination chargers, at the Red Lion Inn, or at Cranwell Spa & Golf Resort — all free.
Three Berkshires itineraries:
- Summer Tanglewood weekend (2-3 days): Friday concert · Saturday brunch at Cafe Lucia · Edith Wharton's Mount · Sunday morning Stockbridge wander
- Peak foliage weekend (3 days): Drive up Friday afternoon · Saturday at MASS MoCA · Sunday hike Mount Greylock summit
- Winter ski weekend (2-3 days): Jiminy Peak skiing · sauna + dinner at Wheatleigh · Sunday at the Norman Rockwell Museum
Where to charge in the Berkshires:
- Red Lion Inn (Stockbridge): Tesla destination chargers in their lot
- Cranwell Spa & Golf Resort (Lenox): Multiple destination chargers
- MASS MoCA (North Adams): Public EV chargers near the museum
- Lee Supercharger: Right off the Mass Pike — your fastest top-up
When to book the Berkshires.
Mid-October
Peak foliage. Book your inn 4-6 weeks ahead — this is the trip people specifically take Tesla Model 3s for. Bring a camera.
Late June – August
Tanglewood season. The BSO's summer home. Lawn tickets are cheap, the music is world-class, and an EV makes the drive home after a concert genuinely relaxing.
Winter weekends
Jiminy Peak skiing, fire-lit lobbies at the Red Lion Inn, MASS MoCA in the off-season (no crowds). The Tesla handles New England snow well.