November and early December in the White Mountains of New Hampshire hit a sweet spot that not enough people take advantage of. The crowds from leaf-peeping season have thinned out, ski season is just warming up, and the towns around Waterville Valley are filling their calendars with live music, holiday traditions, and community celebrations that feel genuinely local. Whether you’re planning a long weekend around a concert or just want a reason to get up here before the slopes get busy, here’s everything worth putting on your radar between November 2 and December 10, 2026.
Monday Nights & Weekend Concerts in November
Trivia Night at The Loft (Every Monday Through Nov 30)
If you’re staying mid-week or stretching a weekend into Monday, Trivia Night at The Loft in Waterville Valley Town Square — literally three minutes from our condo — is a genuinely fun way to spend an evening. It runs every Monday from 7:00–9:00 PM through November 30, with dates falling on November 2, 9, 16, 23, and 30. It’s casual, competitive enough to be exciting, and a great way to meet other people who love this valley as much as you do. Grab dinner at Town Square first and make a full night of it.
Story Songs of the 70s — Friday, November 6, Plymouth
On Friday, November 6, The Flying Monkey Movie House and Performance Center in Plymouth hosts an evening concert celebrating the golden age of the singer-songwriter — think introspective, story-driven folk and pop from the decade that perfected the form. Showtime is 7:30 PM. Plymouth is a short drive from Waterville Valley, and The Flying Monkey is one of those intimate venues where every seat feels like a good one. This one suits couples or anyone who appreciates a mellow, musical Friday night out.
Slambovian Circus of Dreams — Saturday, November 14, Plymouth
A week later, on Saturday, November 14, The Flying Monkey hosts the Slambovian Circus of Dreams — an eclectic psychedelic folk-rock band with a devoted following across New England. Doors open at 6:00 PM and the show starts at 7:30 PM; the event is listed as ages 13 and up, so older kids can come along. This is the kind of live show that’s hard to describe but easy to love. Grab your tickets in advance — this band draws a crowd.
A Holiday Weekend Worth Planning Around (Nov 20–29)
Christmas at The Castle — Nov 20–22 & Nov 28–29, Moultonborough
If you’re looking for a reason to book a Thanksgiving-area getaway in the White Mountains, Christmas at The Castle is it. The historic Lucknow Mansion in Moultonborough transforms into a full holiday showcase across two weekends: November 20–22 and November 28–29. You’ll walk through elaborately decorated rooms, browse a local artisan fair, and warm up with hot chocolate and cookies. It’s self-guided, so you move at your own pace — perfect if you’re traveling with kids or grandparents. Check the Castle in the Clouds website for exact hours before you go, as they can vary by day.
Practical Tips for the Castle Weekend
Moultonborough is in the Lakes Region, roughly an hour from Waterville Valley, so plan for a half-day trip. Arrive early on weekends — the artisan fair draws a crowd and parking fills up. Dress warmly; parts of the estate are outdoors. Pairing this with a Monday Trivia Night back in Waterville Valley Town Square makes for a well-rounded long weekend without a lot of driving.
Early December: Fireworks, Folk Legends & Silent Film
Lincoln Holiday Lights Tree Lighting & Fireworks — Saturday, December 5
The 2nd Annual Lincoln Holiday Lights Tree Lighting & Fireworks takes place at The Mills Marketplace in Lincoln on Saturday, December 5, starting at noon. It’s a free community event — one of those genuinely wholesome afternoons where the whole town shows up, the hot drinks flow, and the fireworks at the end feel like a proper send-off into ski season. Lincoln is close to Waterville Valley, making this an easy day trip. Bring the kids; this one is built for families.
Indigo Girls at Jean’s Playhouse — Friday, December 9, Lincoln
The following Friday, December 9, the Indigo Girls perform in Lincoln at 7:30 PM as part of the Journey to the North Pole concert series, presented by the Believe in Books Literacy Foundation. Tickets start at $79. This is a rare chance to see one of American folk-rock’s most enduring acts in an intimate setting — the kind of show people drive hours for. Snap up tickets early; this will sell out. A great anchor event for a December ski weekend.
Silent Film Series: The Unholy Three — Thursday, December 10, Plymouth
Round out your early December trip with something a little different. On December 10, The Flying Monkey in Plymouth screens The Unholy Three as part of its Silent Film Series. Doors open at 6:00 PM and the screening begins at 7:00 PM. It’s a wonderful, unhurried way to spend a winter evening — classic cinema in a historic venue, the kind of experience that feels nothing like streaming at home. If you’re staying through Thursday after a ski weekend, this is the perfect last-night activity before heading home.
From low-key Monday trivia nights steps from Waterville Valley Town Square to the Indigo Girls performing live in Lincoln, this stretch of November and December in the White Mountains punches well above its weight. Our ski condo at Waterville Valley is the ideal home base — cozy, convenient, and priced from around $119/night for the winter season. Book directly with SNJ Getaway to lock in your dates and start planning the kind of trip that’s worth the drive.
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