Rhode Island and Massachusetts · 3 to 4 days · about 170 miles

Gilded Age New England: Newport to the Berkshires

Mansion-row hotels and country estates.

America's Gilded Age families summered by the sea in Newport and in the hills of the Berkshires. Today their mansions and estates are some of the best places to stay in New England.

Where to stay, night by night

1. Stop 1 · 2 nights

   Newport, RI

   Cliff Walk hotels beside the mansions.

   Our pick: The Chanler at Cliff Walk

   Also worth a look: Castle Hill Inn

   Boutique inns in NewportPrivate homes on Vrbo

2. Stop 2 · 1 night

   Lenox, MA

   Country estates near Tanglewood.

   Our pick: Canyon Ranch Lenox

   Also worth a look: Hotel on North (Pittsfield)

   Boutique inns in LenoxPrivate homes on Vrbo

3. Stop 3 · 1 night

   Stockbridge, MA

   A classic New England village inn.

   Our pick: The Red Lion Inn

   Boutique inns in StockbridgePrivate homes on Vrbo

When to go

June to October; Tanglewood concerts run in summer.

Read the full drive guide

More curated drives