Explore Vermont's Scenic Mad River Valley and Green Mountains on Horseback

By Shawn Hamilton

Autumn is one of the most vibrant and beautiful seasons, and it’s also my favorite time to go horseback riding. With the bugs gone, the air crisp, and the horses feeling fresh and ready to go, it’s the perfect opportunity for a memorable trail ride. There’s nothing quite cantering through the woods while the brilliant reds, oranges, and yellows of fall leaves rush by. Living in Ontario, we’re known for our stunning autumn landscapes, but a short trip across the border to Vermont reveals the rolling hills of the Green Mountains, offering an equally breathtaking sight.

For the ultimate autumn experience, there's no better way to enjoy Vermont's fall colors than from horseback. After some research, I discovered two must-see locations in the Green Mountain State where you can take in the vibrant foliage while riding. This past October, I packed up my gear, grabbed my riding companion Cinette, and headed south to immerse ourselves in Vermont’s fall splendor.

Our first destination was the Vermont Icelandic Horse Farm, located in the picturesque Mad River Valley. Situated on 45 acres near Waitsfield, this farm offers the perfect setting to enjoy the fall season from the saddle. Waitsfield itself, established in the early 19th century, was once the commercial hub for local farming communities. The village is home to two iconic covered bridges: the Great Eddy Bridge, built in 1833, and the Pine Brook Bridge, which dates back to 1872. These historic structures are part of Vermont's covered bridge legacy, with around 100 still standing today, showcasing the craftsmanship of the 19th-century bridge builders.

For a horseback riding adventure amidst Vermont’s stunning fall colors, the Vermont Icelandic Horse Farm in the Mad River Valley offers an unforgettable experience, combining scenic beauty, rich history, and the joy of riding through nature’s autumn canvas.

The naturally-gaited Icelandic horses at Vermont Icelandic Horse Farm are a pleasure to ride. Photo: Clix Photography

The Pine Brook Bridge crosses Pine Brook in Waitsfield, Vermont, one of two historic covered bridges in the town. Photo: Shutterstock/Reimar

Here at the Vermont Icelandic Horse Farm, not only can you experience the pageantry of Vermont’s seasonal colour, you can ride a truly magnificent breed of horse — the naturally gaited Icelandic, one of the oldest breeds in the world — while enjoying the culture and history of the area. These little horses are bred to move freely and smoothly along difficult terrain. Their unique free-flowing and effortless gait, the Tölt, floats the rider along the trail. They are patient, have a positive attitude, and thanks to their efficient movement they have tireless energy, making them well-suited for trail riding. Standing from 12 to 14 hands high, Icelandic horses have a stocky frame, allowing them to carry up to one third of their body weight.

Upon our arrival at the Vermont Icelandic Horse Farm, owner Karen Winhold emerges from the small barn built underneath the house, both designed and constructed by her father, Otto Winhold. Once the guests have arrived, the horses are assigned, stirrups are adjusted, girths tightened, and everyone makes their way up the driveway on their trusty Icelandic horse. All of Winhold’s horses are direct descendants of Icelandic pure stock, and she prides herself on their character.

“Icelandic horses are naturally people-oriented and friendly, their character is number one. Their willingness to tolerate so much, combined with their easygoing personality, makes them a perfect match for any trail enthusiast,” says Winhold.

The morning ride starts from the stables and heads to an ancient spring-fed watering trough where the horses stop for a refreshing drink. Further up the road, the ride passes an old 1813 school, now housing a local artist. A turnoff into the woods offers a magnificent view of the valley below, with the Green Mountains proudly displaying their fall colours. The ride continues on with a combination of road and forest trails, passing ski chalets and sheep farms, crossing rivers and streams, then returns to the farm for lunch. Visitors can choose between a half or full day of riding, or the longer two- to six-day package on the lovely four- and five-gaited Icelandic horses. 

The horses stop for a drink at an ancient spring-fed water trough. Photo: Clix Photography

Mad River Inn, circa 1860, is a renovated inn located six miles from the Vermont Icelandic Horse Farm in the historic town of Waitsfield. Photo: Clix Photography

Karen and her husband Luke, a French Canadian, operate the Mad River Inn just six miles down the road from the horse farm. Guests can relax in one of the cosily-decorated guest rooms and enjoy the tasty meals Luke creates. A homemade breakfast in the Queen Anne furnished dining room starts off an enjoyable day in the saddle. After riding, guests can sip tea on the porch or soothe tired muscles in the hot tub. It is a truly delightful and relaxing atmosphere.

Our second stop is the prestigious Mountain Top Resort, located just outside the small town of Chittenden, Vermont, conveniently located near the Killington ski area. This luxurious resort offers 40 miles of trail riding on the property, combined with access to parkland. The hilly trails double as a cross-country ski park in the winter. Arriving just after sunset, we are greeted by the friendly front desk clerk who directs us to our room. The hallway is laden with photos of famous people who have stayed there, from Dwight D. Eisenhower to Jennifer Aniston. The room is spacious and well-appointed with a fireplace and jacuzzi tub. We quickly unpack to find our bathing suits, and head to the hot tub for a soak under the stars. After an exquisite dinner in the restaurant, we retire to comfy beds and look forward to tomorrow’s adventures.

Making memories in Vermont’s beautiful fall foliage. Photo: Clix Photography

Unfortunately, Mother Nature has another plan and we awake to rain. We walk to the stables to meet the barn manager, Louise, and with hopes that the weather will clear up in the afternoon, she invites us to tour the stables. The tack room is lined with saddles, each labelled with their purpose and size, and girths each displaying their length. In my travels, I had never seen an operation organized this way, and was quite impressed. The barn is simple with box stalls easily doubling as two standing stalls with a removable divider. The farrier is shoeing a horse in the wide aisle as Louise tells me that a large percentage of the horses are leased. Once the snow flies, they head back to their home farm, or head out to their winter job. Only a handful stay during the ski season, including their draft horses who take guests for the romantic snowy sleigh ride experience. 

ABOVE and BELOW: The patient, people-oriented temperament of the Icelandic horses makes it easy to relax and enjoy the scenery. Photos: Clix Photography

By noon the rain has stopped, and we head to the barn to meet our mounts. I am presented with Chip, aptly named for the small slice out of his left ear. Cinette will ride Hershey, a Thoroughbred used on the off-season by a private college for their equestrian program. Due to the slippery trail, we wind slowly up the mountainside, with the fog hanging in the air among the trees, providing a mystical backdrop. Joining us are two other guests, and the ride is at a slower pace because they are beginners. The views are fogged in, so we head down the mountainside to the beach beside the 740-acre lake, where a pontoon boat awaits tourists who wish to take a ride. A pavilion is provided for private events by the lake. Mountain Top Resort is well-equipped for weddings, with options ranging from outdoor lakeside or mountain views, to private indoor facilities. We cross a winding stream and return to the inn with high hopes that the weather will improve by tomorrow. 

The next morning dawns with a hint of blue in the horizon. After breakfast we claim our mounts for the morning ride. Cinette is pleased to have Hershey again as he responds well to her aids, a testament to his work in the off-season. My horse today is Pokey, a chestnut with a white blaze.

Moments after leaving the barn, the views open up and we can see down to the lake. Today, it’s just the two of us and our guide, Marissa, so we are hoping for a few canters. As we head out onto the trail going up to the mountain to enjoy the vistas below, we pass a small pond offering reflections of the coloured leaves. Winding further up the hill, signs displaying the level of difficulty of the cross-country ski trails line the intersections. At the top, the forest opens up displaying the fall colour of the rolling Green Mountains surrounding the lake. We rest for a moment to take in the spectacular view. 

ABOVE: Mother Nature paints the foliage of Vermont in yellows, reds, and oranges from mid-September until late October, moving from north to south and from higher to lower elevations. Photos: Clix Photography

As we head down the mountain, Marissa tells us that Mountain Top Resort allows horse owners to bring their own horses to stay on the property, and groups can rent one or more of the many houses in the vicinity. Cinette and I are already making plans to return for a cross country ski weekend, and to invite our other horsey friends for a fun week of riding our own steeds on these lovely trails.

Once down the mountain, we ride through the wide, open green space where a wedding party is setting up. We head down the road to the lake, then open up the horses to a full canter as we climb back up to the resort. The horses flow into canter with ease as the reds, yellows, and oranges whiz by. This is what we came for, and Mountain Top Resort delivered. Upon returning to the barn, we thank our horses and all the people who showed us such a wonderful time. We are sad to leave, but we know in our hearts that we will return next fall with our own horses in tow. 

The author with Pokey, one of her mounts at the Mountain Top Resort. Photo: Clix Photography

Check out more Holidays on Horseback.

Read more by Shawn Hamilton

Main Photo: Clix Photography