A Berkshires Holiday Weekend in Lenox

The Berkshires in December are a different place than the Berkshires in July. The Tanglewood crowds are long gone, the roads are quiet, and the hill towns turn their attention to the thing New England does better than anywhere else: a proper, unhurried holiday season. If you have been meaning to get up here and the summer calendar never cooperated, this is the window.

Here is how to put together a Berkshires holiday weekend in Lenox — what to see, where to eat between, and why staying in the village itself makes the whole thing easier.

Winterlights at Naumkeag

The anchor of the season. Naumkeag, the Gilded Age estate in neighboring Stockbridge, wraps its terraced gardens in hundreds of thousands of lights and opens them after dark. The Blue Steps — the estate’s signature run of fountains and birch trees — are the photograph everyone comes for, but the quieter stretches of the garden path are the reason to linger.

It is about a fifteen-minute drive from the hotel. Winterlights tickets are timed and the early-evening slots on weekends go first, so book as soon as they are released rather than the week you travel.

Tip: dress for standing still, not for walking. The gardens are exposed and you will want to stop a lot more than you expect.

A Gilded Age Christmas at Ventfort Hall

Ventfort Hall is a short walk from Main Street — the 1893 Jacobean Revival mansion built for Sarah Morgan, J.P. Morgan’s sister. In the holiday season the house is decorated in period style and opened for tours that lean into how the Gilded Age families actually kept Christmas in the Berkshires. 

It pairs naturally with Naumkeag: one is the estate outdoors at night, the other is the house indoors by day. Do them on the same weekend and the period thread between them is hard to miss.

Holiday shopping in Lenox village

Lenox does not need a program to be worth a December afternoon. Church Street and Main Street hold a tight cluster of independent shops — books, antiques, housewares, a couple of galleries — and in the weeks before Christmas it is genuinely good browsing rather than a tourist stroll. 

Worth working in if the weather holds: the trails at Kennedy Park start at the top of the village, and a loop through the snow before dinner is the cheapest luxury of the whole weekend.

Where to eat in Lenox

• Before Winterlights — something early and unfussy in the village, since timed tickets rarely line up with a leisurely dinner. Frankie’s Ristorante Italiano on Main Street is the right fit for a lighter Italian dinner.
• The one real dinner — book this for the Saturday and book it ahead. Winter is quieter, but the good rooms in Lenox still fill on a Saturday. Our pick is Bea’s House on Church Street.
• Sunday before the drive — a long breakfast and a bakery stop for the road. Haven Cafe & Bakery on Franklin Street covers both.

A two-night shape that works

• Friday — arrive late afternoon, walk the village, early dinner, settle in.
• Saturday — Ventfort Hall or the shops in the morning, a walk in the afternoon, Winterlights after dark, late dinner.
• Sunday — breakfast, one last stop on Main Street, home by mid-afternoon.

Midweek is the quiet version of the same weekend, and usually the better-value one. If your schedule allows a Sunday-through-Tuesday instead, take it.

Staying in the village

Garden Gables sits on Main Street in Lenox, on several acres a few minutes’ walk from the shops and restaurants — which matters more in December than it does in August. You can park the car on Friday and leave it there except for the run over to Stockbridge. 

Holiday weekends book earlier than the rest of the winter, and the Winterlights weekends book earliest of all.

Check winter availability and current offers

Planning further out? See also: Christmas in the Berkshires: A Lenox Guide to Winterlights, Stockbridge, and the Quiet Season and A New Englander’s Guide to the Berkshires After the Leaves Fall.