Thanksgiving in the Berkshires: How to Plan the Long Weekend in Lenox

Thanksgiving falls on Thursday, November 26 this year, and the week of it the Berkshires are a different place than they were in October. The leaf traffic on Route 7 is gone. The restaurants that were booked three deep in August have tables again. And for four days the whole valley does more or less what we do here at the inn, which is eat too much, walk it off, and then go back for pie.

Here is how we would plan the weekend.

Book the meal before you book anything else

If you would rather someone else cooked, reserve now. Thanksgiving tables go before the rooms do.

Close to home, most Lenox kitchens post their holiday plans in the second week of November. Call rather than check a website. A Thanksgiving menu is the last thing a restaurant puts online and the first thing it sells out of.

And if you would rather eat in: the village markets take orders for sides and pies well ahead of the holiday, and our guests have been known to carry a pie back up the stairs and finish it in a bathrobe. We think that is a perfectly good Thanksgiving.

Friday belongs to Winterlights

Naumkeag opens Winterlights on Friday, November 27, the day after Thanksgiving, and runs it through January 2. The terraced gardens of the Choate estate in Stockbridge, the next town south, get lit end to end. Walking them on the opening night of the season, with the leftovers still in the fridge, is close to the best thing the Berkshires do in November.

Buy ahead, because this one catches people out. Tickets are timed and sold in advance only, and nothing is sold at the gate. Adults are $32, children 3 to 15 are $15, and Trustees members pay less. Gates run 4:30 to 9 p.m., Wednesday through Sunday. Parking is off site and you choose your zone when you book, either downtown Stockbridge, the Playhouse, or the Pine Street lot at Marian Fathers. Shuttles leave every five to ten minutes until 8, and the last ride back is at 9. There are no drop-offs at the main gate, and parts of the route are not stroller or wheelchair friendly.

Dress for standing still outdoors, not for walking. There is a difference in late November, and everyone learns it once.

Saturday is for walking it off

The trails around Lenox are at their best the week after the leaves come down, when you can finally see the shape of the hills through the trees. Kennedy Park starts right at the top of Main Street, which means you can walk to the trailhead from the inn, do an hour on the carriage roads, and be back before anyone notices you left.

Then Church Street. The shops are small and independently owned, the Saturday after Thanksgiving is one of their best days of the year, and buying a gift there instead of online is the single most useful thing a visitor can do for a Berkshires village in winter.

Sunday is for leaving slowly

The mistake people make with a Thanksgiving weekend here is treating Sunday as a travel day. Nothing in the valley is in a hurry that morning. Have the long breakfast, take the back road out through Stockbridge rather than the highway, and stop at least once.

Why we like this weekend best

We will say the quiet part out loud: Thanksgiving weekend is the one holiday weekend in the Berkshires where you can still get the room you actually want. December books up around Winterlights and the Christmas traffic. August is August. The last week of November is the one stretch where the valley is full of things to do and not full of people.

Garden Gables has eleven rooms on five acres, a ten-minute walk from the Lenox restaurants and the Church Street shops, which matters more than usual on a weekend when nobody wants to drive after dinner. The fires are lit. Breakfast is at a reasonable hour.