Some of the best hours of a Killington vacation happen at a walking pace. In winter, that means bells on a harness and a wool blanket over your knees as a pair of draft horses pulls you across a snowy meadow. From late spring through fall, it means a guided trail ride through hardwood forest with the Green Mountains opening up between the trees. Both are within an easy drive of your rental, and both are the kind of thing families and couples talk about for years.

This guide is split by season so you can find what is running when you visit: sleigh rides near Killington for the winter months, horseback riding near Killington from May through October, what to expect on a first ride, and a full day plan that pairs the ride with lunch and a sunset.

The Gallop (Rundown)

The closest full-service option for both is Mountain Top Inn & Resort in Chittenden, about 30 minutes from Killington, which runs horse-drawn sleigh rides from late December through March (book ahead by phone) and guided one- and two-hour trail rides from Memorial Day weekend through October, with pony rides for younger kids. Pond Hill Ranch in Castleton offers hour-long trail rides by appointment year-round plus Saturday-night summer rodeos, and Billings Farm in Woodstock adds private sleigh rides in winter. Riders on trail rides generally need to be 8 or older; sleigh rides welcome all ages.

Winter: sleigh rides (book ahead)

A horse-drawn sleigh ride is the rare winter activity that works for a toddler, a grandparent and a couple on a date at the same time. It is also the one Killington activity that sells out quietly, because rides run in small groups and the holiday weeks fill first. Book it the same week you book your home.

Mountain Top Inn & Resort, Chittenden

Mountain Top's sleigh rides run from late December through March, weather and snow permitting, and they are open to the public, not just resort guests. Rides last about 30 minutes across the resort's high meadows above Chittenden Reservoir, and you can book a private sleigh for your own group (up to nine people) or reserve seats on a shared ride, with per-person rates for adults and children and the youngest riders free. Reservations are by phone, and the resort charges half the ride price for cancellations inside 24 hours, so plan around the weather forecast rather than the calendar. As of fall 2026, a private 30-minute sleigh was listed at $400 and shared-ride seats at $50 per adult and $25 per child; confirm current rates when you call.

The drive from Killington is about 30 to 35 minutes, and Mountain Top's tavern and dining room overlook the lake, which makes lunch after the ride an easy decision (more on that below).

Billings Farm & Museum, Woodstock

Billings Farm, about 30 minutes east of Killington, offers private 30-minute sleigh rides from December through March. Reservations typically open in November and the farm asks for about two weeks' notice, and if the snow does not cooperate the horses pull a wagon instead. On winter operating days the farm also runs short public sleigh rides for a few dollars per person on top of admission, an easy add-on to a museum visit with kids.

Kedron Valley Stables, South Woodstock

Kedron Valley Stables offers sleigh rides in winter and carriage rides in summer for private groups by arrangement. Call ahead for availability and pricing; the stable does not publish a public schedule.

Good to know: Killington Resort itself does not run horse-drawn sleigh rides. The mountain's winter extras are the tubing park, the gondola and the après scene, so for horses you will head to Chittenden or Woodstock.

May to October: trail rides and rodeo nights

Once the trails dry out, the same hills that host sleigh rides become some of the best riding country in Vermont. Two operators cover most of what visitors want.

Mountain Top Inn & Resort: guided trail rides

Mountain Top's equestrian center is open to the public from Memorial Day weekend through October and offers guided one-hour and two-hour trail rides through the resort's forest and meadow trails. Riders must be at least 8 years old and 48 inches tall, and helmets are required. The one-hour ride is the right call for first-timers and families; the two-hour ride reaches the higher viewpoints and suits anyone who has ridden before. As of fall 2026, one-hour rides were listed at $55 per person and two-hour rides at $100, with 15-minute pony rides for younger children at $25. The season start can shift with the weather, so call before you plan a Memorial Day ride.

Pond Hill Ranch, Castleton: trail rides and the rodeo

Pond Hill Ranch is a working ranch about 45 minutes west of Killington, on the far side of Rutland. Guided trail rides last about an hour, are open to riders 8 and older and run seven days a week by appointment, with pony rides for younger kids and English or Western lessons if someone in your group wants to go deeper. The ranch is known for taking beginners out comfortably.

The other reason to make the drive is the rodeo. Pond Hill has produced summer rodeos for more than 50 years, and the current series runs Saturday nights at 7:30 from the Fourth of July weekend through Labor Day weekend, rain or shine. Admission is cash at the gate (around $15 for adults as of 2026, less for kids), and it is one of the most fun evenings you can give a family in Vermont: bull riding, barrel racing, roping and a grandstand full of locals. Bring a sweatshirt; it cools off fast after sunset.

Sleigh rides and trail rides near Killington at a glance

• Mountain Top Inn & Resort, Chittenden. Season: Sleigh: late Dec to March. Trail: Memorial Day to October. What they offer: 30-min private or shared sleigh rides; 1- and 2-hour trail rides; pony rides. Minimum age: Sleigh: all ages. Trail: 8 and 48 in. Drive from Killington: About 30 to 35 min.

• Pond Hill Ranch, Castleton. Season: Trail rides by appointment, seven days a week (call for seasonal availability); rodeo July to early Sept. What they offer: 1-hour trail rides, pony rides, lessons, Saturday rodeo. Minimum age: Trail: 8. Drive from Killington: About 45 min.

• Billings Farm & Museum, Woodstock. Season: Sleigh: Dec to March. Wagon: fall. What they offer: Private 30-min sleigh rides; short public sleigh and wagon rides. Minimum age: All ages. Drive from Killington: About 30 min.

• Kedron Valley Stables, South Woodstock. Season: Sleigh in winter, carriage in summer. What they offer: Private rides by arrangement. Minimum age: Ask. Drive from Killington: About 35 min.

Prices, hours and minimums change season to season; treat the details above as a planning guide and confirm with the operator when you book.

What to expect on a first ride

Never been on a horse? You are the exact rider these operators are set up for. A few things make the first ride better.

• Attire. Long pants (jeans are perfect), closed-toe shoes or boots with a low heel, and layers you can shed. In fall, add gloves and a warm hat that fits under a helmet. Leave the sandals and the flowing scarf at the house.

• Helmets. Mountain Top requires a certified riding helmet for all riders. Wear the one they hand you; it is not optional and it is not a style question.

• Weight limits. Most trail-ride operations set a rider weight limit for the horses' welfare, commonly somewhere around 200 to 250 pounds. Ask when you book so nobody is surprised at the barn.

• Private vs. group. Shared rides are the standard and the price is per person. If you want your own guide, a proposal moment or a nervous rider's full attention, ask about a private ride; on quiet days you may get one by luck.

• Photos. Ask your guide before you pull out a phone. Most are happy to stop at a viewpoint for a photo, and most will also tell you to keep the phone zipped away while the horses are moving. A wrist strap or a zip pocket is the answer.

• Tipping. Guides work hard for a walking-pace hour with beginners. A tip in the 15 to 20 percent range is customary and appreciated.

For sleigh rides, the only prep is warmth: snow boots, a hat, mittens and a thermos. The blankets are provided, and the cold is half the charm.

A ride, lunch and sunset day plan

The best version of this outing is a full day built around Chittenden, which sits just north of Killington in a valley that feels a world away from the ski road.

1. Morning: ride at Mountain Top. Book the first sleigh ride of the day in winter, or a 10 a.m. one-hour trail ride from June through October. Arrive 15 minutes early to sign waivers and meet your horse.

2. Midday: lunch overlooking the lake. Mountain Top's tavern and dining room serve lunch daily in season with a view over Chittenden Reservoir, and both are open to the public. If you would rather eat in town, Rutland is 20 minutes back down the hill; our guide to the best Rutland restaurants has options for every appetite.

3. Afternoon: Lefferts Pond and the reservoir. Spend the afternoon at Lefferts Pond, the quiet pond beside Chittenden Reservoir with an easy loop trail, fishing and paddling in summer and snowshoeing in winter. It is one of the calmest spots in the region.

4. Sunset: Chittenden Reservoir. Stay for the sunset over the water, then drive the 30 minutes back to your Killington home for the hot tub. In summer, bring bug spray; in winter, bring the thermos again.

Couples, take note: a private winter sleigh ride followed by dinner is the single most romantic afternoon on our list of romantic getaways in Vermont. For more on the wildlife and scenery you will pass on the trail, see our Killington nature and wildlife guide.

The family angle: pony rides and kid minimums

The number to know is 8. Both Mountain Top and Pond Hill set 8 as the minimum age for guided trail rides (Mountain Top also requires 48 inches of height), which is about the age a child can sit a saddle, follow a guide's instructions and enjoy an hour on a horse rather than endure it.

Younger kids are not left out. Both operators offer pony rides for kids with a handler leading the pony, which for a five-year-old is every bit as thrilling as the real thing. Sleigh rides have no minimum age at all, and a lap-sized child rides free at Mountain Top. In summer, the Pond Hill rodeo is a family evening with no age limit and a snack stand, and Billings Farm pairs its wagon rides with a working dairy farm that kids can explore.

Pack for the kids the way you would for a hike: layers, snacks, water and a change of clothes for the barn smell, which is real and which they will love. For more ideas, our post on things to do with children in Killington rounds out the week.

Slow down. The mountain will still be there.

Killington is a place that rewards speed: first chair, fast laps, a full itinerary. The horses are the antidote. A sleigh moves at a walk, and so does a trail ride, and for an hour the only sounds are hooves in the snow or leaves under the trail and a guide pointing out where the moose crossed last week. It is the slowest hour of the trip, and years later it is often the one the kids bring up first, along with the pony's name.

The only work involved is booking it, and the earlier the better in a holiday week. Call Chittenden or Woodstock the same day your home is confirmed, dress for the barn, and leave the afternoon open for lunch by the lake and a sunset over the reservoir. Couples, book the private sleigh and do not tell anyone why. Families, take the pony ride for the little ones and the trail ride for the eight-and-ups, and let the rodeo be the surprise on Saturday night.

Then drive the 30 minutes home, put the kettle on, and get into the hot tub while the smell of the barn fades from everyone's coats. That is a Vermont day done right, and we would love to host the rest of the week around it.

Book the home, then book the horses

Our Killington rentals put you 30 minutes from the sleigh bells in Chittenden and a hot tub away from the end of the day. Find your home, then call the barn.

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Frequently asked questions

Where can I take a sleigh ride near Killington, Vermont?

The closest options are Mountain Top Inn & Resort in Chittenden (about 30 minutes) and Billings Farm & Museum in Woodstock (about 30 minutes), both of which run horse-drawn sleigh rides from roughly late December through March, weather permitting. Kedron Valley Stables in South Woodstock offers private sleigh rides by arrangement. Book ahead; holiday weeks fill early.

How far in advance should I book a sleigh ride?

For Christmas week, Martin Luther King weekend and Presidents' Week, book two to four weeks ahead, or as soon as your lodging is confirmed. Billings Farm asks for about two weeks' notice for private rides. On a normal January or February weekend, a few days' notice is often enough, but rides run in small groups, so earlier is always safer.

How old do kids need to be to go horseback riding near Killington?

Eight years old for guided trail rides at both Mountain Top Inn and Pond Hill Ranch, and Mountain Top also requires riders to be at least 48 inches tall. Younger children can take a handler-led pony ride at either operator, and sleigh rides welcome all ages.

When is horseback riding season in Vermont?

Mountain Top's trail rides run from Memorial Day weekend through October, with the exact start depending on how quickly the trails dry after mud season. Pond Hill Ranch offers trail rides by appointment seven days a week; call for seasonal availability. Late September and early October, when the foliage peaks, is the most beautiful window.

Do I need riding experience for a trail ride?

No. One-hour guided rides at Mountain Top and Pond Hill are designed for beginners, with calm horses, a guide leading the group and a walking pace throughout. Wear long pants and closed-toe shoes, wear the helmet you are given, and tell the guide it is your first time so they can match you with the right horse.

What is the Pond Hill Ranch rodeo?

A summer rodeo series in Castleton that has run for more than 50 years, held Saturday nights at 7:30 from the Fourth of July weekend through Labor Day weekend, rain or shine. Events include bull riding, barrel racing and roping. Admission is cash at the gate, and it is a favorite evening out for families staying in Killington.