Mount Snow is a fantastic mountain just 20 minutes away.
We highly recommend the Harriman Reservoir (photo below), which is 7 minutes away and absolutely gorgeous. Lake Raponda is also beautiful with a beach for easy entry and a floating doc that's fun for jumping in.
We have a bunch of rustic trails on our property (probably ~2.5 miles of trails), including the photo below. Directly across the street from our driveway is the Shearer Hill Trailhead, a county trail that takes you to Mt. Olga and connects to the trails in Molly Stark State Park. Molly Stark State Park is a 6 minute drive with very pretty hikes that are fun for both adults and children. There's also a very mellow hike right in Wilmington called the Hoot Toot and Whistle Trail that meanders along a river. Jamaica State Park is about 45 minutes away with a beautiful river and great hiking. Here's a local map: https://wilmingtonvermont.us/wp-content/uploads/2013/11/Wilmington-Trail-Map.pdf
* Aside from the game room and hot tub, we have a ton of board games, DVDs including kid-friendly ones downstairs, a pool table in the garage, a device that has a ton of games from before 2000 (more than 100,000 games!) that you can play on the TV in the upstairs living room. * Escape room (https://mindlockescaperoom.com/) Dover, 15 min away * Movie theater (https://www.memhall.org/) - Dover, 15 min away * Candlepin bowling and mini golf at North Star Pizza (https://www.facebook.com/profile.php?id=100067679977553) - 15 min away * Paint & Sip - Arthouse, call to check availability (https://www.arthousevt.com/) Wilmington, 7 min away * The Last Chair Restaurant has a small arcade (great if you are going for a meal) - Dover, 20 min away * Snow Republic Brewery has shuffleboard, pool, and other games - Dover, 15 min away * Sprague and Son sugar shack - taste maple syrup tasting (this is a 10 min jaunt, but fun! Call to make sure they're open.) * MASS MoCA, 45 min away * Manchester: Pasttime Pinball (https://pastimepinball.com/), Lincoln's family home (https://hildene.org/), and this amazing bookstore (https://www.northshire.com/manchester-store). * Bennington and Brattleboro are both cute towns about a half hour away. Brattleboro has this cute museum: https://www.brattleboromuseum.org/ and pinball place: https://gravitatepinball.com/ and Bennington has a museum: https://benningtonmuseum.org/ - Not exactly what you asked, but there's a great private chef who can come cook a meal at the house - while it would not get you out it's a way to change things up while being inside.
- Farm Road Estate sets up an ice skating rink. Call ahead to make sure it's open!
Snowmobile Vermont (snowmobilevermont.com) runs highly recommended tours! Our property also connects to the VAST network.