The Short and Sweet Tour allows you to embark on an unforgettable three-day bike tour through the scenic landscapes and rich cultural heritage of Woodstock, Vermont. Nestled in the heart of New England and known for its breathtaking landscapes, rich cultural heritage, and remarkable people, Woodstock offers an idyllic destination for adventure travel enthusiasts. In this blog, we will delve into the captivating world of small town Vermont, Woodstock’s enchanting history, culinary delights, remarkable places, and the unparalleled warmth of its hospitality. Woodstock is steeped in history, and as you pedal through its streets, you’ll feel as though you’ve stepped back in time. The town’s rich heritage is evident in its well-preserved architecture, including historic homes and buildings. One iconic symbol of Woodstock’s history is its covered Middle Covered Bridge, an architectural classic that dates back to 1969, built by Milton Graton to replace an 1877 iron bridge. As you ride across this picturesque bridge, you can’t help but imagine the countless travelers who have crossed its wooden planks. This section connects the village to Mountain Avenue and the foot of Mt. Tom, which overlooks the village. The tour is bookended by iconic, covered bridges as we’ll cross the Taftsville Bridge on day three on our way to Simon Pearce, a renowned glass blowing factory in Quechee, Vermont.

If you’re seeking an exhilarating outdoor experience, replete with history, culture and a vibrant sense of connection to the ecology and land of Vermont, you’ll be thrilled with this tour. This boutique experience allows you to immerse yourself in the region’s natural beauty while discovering its fascinating cultural heritage. From leisurely rides through picturesque countryside to more challenging routes for seasoned cyclists, Woodstock has something for everyone.

One of the highlights of this bike tour is the opportunity to explore the rich history of Woodstock, Pomfret, and surrounding towns and villages. You’ll ride past Billings Farm & Museum, a captivating working farm that offers a glimpse into Vermont’s agricultural heritage. Billings Farm & Museum is a prominent working farm located in Woodstock itself. This historical treasure allows visitors to experience firsthand the daily activities of a late 19th-century dairy farm. The farm is complemented by the adjacent Marsh-Billings-Rockefeller National Historical Park, dedicated to environmentalism and the legacy of Laurence Rockefeller, one of the town’s many grand land stewards. The park’s stately grounds contain pristine landscapes, lush forests, and picturesque trails, all of which provide insight into the region’s commitment to land conservation, sustainable practices, and the importance of preserving nature for future generations. On day two, we will venture to nearby Plymouth, Vermont, where Calvin Coolidge, the 30th President of the United States. was born and raised. Visit the Plymouth Cheese Factory, which has been producing delectable artisanal cheeses since 1890. Delve into history further by touring the Calvin Coolidge State Historic Site and stepping back in time to the era when Coolidge was in office. Discover the simple, rural lifestyle that shaped his character and presidency. We’ll have the opportunity to sample artisanal cheese at Plymouth Cheese, in the very building Coolidge’ father set up a cheese factory in 1890. You’ll have the opportunity to rest your legs after pedaling at Long Trail Brewery, situated in Bridgewater Corners near Woodstock, renowned for its exceptional craft beers. With a dedication to quality and a passion for brewing, Long Trail offers a range of delicious and distinct brews. They were on the front end of the micro-brew and craft beer revolution that can be experienced across Vermont today- another testament to the state’s many locally sourced and high quality, artisanal products like Ben & Jerry’s Ice Cream.

The region’s picturesque landscapes provide the perfect backdrop for an unforgettable biking experience. As you explore the countryside, you’ll be treated to breathtaking vistas of rolling hills, serene farmland, and the majestic peaks of the Green Mountains, including Mt. Killington, the second highest peak in Vermont. The winding country roads will lead you through a series of charming New England villages, where you can take a break and interact with the friendly locals as we re-hydrate and fuel up for another ride.

Throughout your scenic journey you’ll continually ride along and over the Ottauquechee River, which meanders through the heart of Woodstock. We’ll follow the river as it flows past covered bridges and bucolic meadows, immersing yourself in the tranquility of the surrounding nature. Our loop routes will guide the group tour through sweeping valleys and dense forests. Quechee Gorge, often referred to as “Vermont’s Little Grand Canyon,” is a breathtaking natural wonder located just a short distance from Woodstock. Carved by the Ottauquechee River over thousands of years, this magnificent gorge offers visitors a mesmerizing display of rugged cliffs, cascading waterfalls, and panoramic views that leave a lasting impression. As you approach Quechee Gorge, the first thing that strikes you is the dramatic sight of the 165-foot-deep chasm, with its walls adorned in shades of rust, green, and grey. The Quechee Gorge Bridge, an architectural marvel, spans the gorge and provides a picturesque vantage point for admiring the beauty of the surroundings. Walking along the bridge, you can’t help but marvel at the sheer grandeur of nature that unfolds before your eyes. The trail also provides access to the river, where you can dip your toes in the cool waters after a full weekend of revitalizing rides.

As you pedal through the countryside, you’ll discover hidden waterfalls, secret swimming holes, and roadside stands selling fresh produce and homemade treats. These unexpected gems add an element of surprise and discovery to your biking adventure. Woodstock’s scenic biking routes cater to riders of all skill levels, from leisurely riders seeking a relaxing journey to more experienced cyclists looking for a challenging workout. We provide fully supported rides, suitable for experienced riders looking for elevation climbs and challenges as well as the flexibility to those looking to absorb the Vermont landscape at more intermediate speeds. The village and its surrounding areas are blessed with a thriving agricultural landscape, where farms play a vital role in shaping the region’s character and providing fresh, local produce. We pedal past dozens of stunning farms throughout the three day adventure.

One of the many organic farms we ride pass is Cloudland Farm in Pomfret. This stunning farm boasts rolling pastures, scenic views, and a commitment to sustainable farming practices. Their herd of grass-fed Angus cattle graze on lush fields, resulting in tender and flavorful beef. You can purchase their premium meats at the farm store or savor their culinary creations at one of the local restaurants we frequent. Jennie’s Farm, located just outside of Woodstock, offers a picturesque setting with rolling pastures, friendly farm animals, and the opportunity to pick your own fresh produce. Throughout the seasons, thousands of photographers from across the globe descend to shoot this postcard perfect scene. Most of these farms are family-owned and operated and prioritize sustainable agriculture and community involvement. Their extensive variety of vegetables, fruits, and herbs are grown using organic practices, providing a bounty of flavors to local restaurants and farmers’ markets. In nearby Barnard, we sometimes frequent Earthwise Farm & Forest, a diversified organic farm specializing in pastured pork and poultry. This farm not only raises animals using sustainable methods but also offers educational programs and workshops on homesteading, permaculture, and regenerative farming practices. It’s a great place to learn about holistic approaches to agriculture while enjoying the beautiful surroundings. Each of these distinct farms contribute to the region’s vibrant agricultural community, offering fresh, local products and fostering a deep connection to the land. During your visit, we’ll explore these farms, interact with the farmers, and savor the flavors of Vermont’s bountiful harvest.

After an eventful and fully curated day of biking and exploration, find solace at the classic Kedron Valley Inn. Nestled amidst breathtaking surroundings, this inn offers comfortable accommodations, warm hospitality, and a perfect ambiance to revitalize yourself for the next day’s adventure. We’ll ndulge in their farm-to-table cuisine, featuring locally sourced ingredients, and savor the flavors that reflect the true essence of Vermont. Take a leisurely stroll around the inn’s beautifully landscaped gardens or relax on the porch with a refreshing drink in hand. The Kedron Valley Inn embodies the spirit of Woodstock, providing a tranquil retreat where you can recharge and connect with nature.

Woodstock, Vermont, is a destination that captures the hearts of all who visit. From its remarkable people and remarkable places to its vibrant local culture and cuisine, every aspect of this charming town will leave you inspired. Whether you’re seeking an adventure-packed multi-day bike tour, a chance to delve into history, or simply a serene ride through scenic landscapes, Woodstock has it all. Explore the town’s captivating history, indulge in its culinary delights, and bask in the warm hospitality of its locals. A guided, vigorous vacation in Woodstock promises not only a revitalizing experience but also an opportunity to connect with nature, appreciate the region’s cultural heritage, and create lasting memories. So, hop on your bike, embark on an unforgettable journey, and discover the true essence of Woodstock, Vermont.