Day 1:

• 8:00 AM – 9:00 AM: Arrive in Windsor, Vermont, starting your trip with a coffee and breakfast at The Windsor Diner.

• 9:30 AM – 11:00 AM: Explore downtown Windsor and take part in a self-guided Architectural and Historical Walking Tour, a self-guided exploration featuring over 40 historic structures that showcase the town's rich architectural heritage. The tour includes landmarks such as the Old Constitution House, where Vermont's constitution was signed in 1777, and various buildings reflecting Federal, Greek Revival, and many other 19th and 20th century styles.

• 11:30 AM – 5:30 PM: Choose from the following:

  • (1) Take a short drive north to Artisans Park for a delightful afternoon. Watch master glassblowers at work and browse handcrafted glassware at Simon Pearce, then stop by Blake Hill Preserves to sample award-winning jams and explore their selection of over 40 artisanal preserves. Sip craft cocktails or try a tasting flight at SILO Distillery, known for its Vermont-made small-batch spirits. Enjoy locally brewed beers, ciders, and pub-style fare at the Harpoon Brewery Taproom and Beer Garden, where the dog-friendly outdoor space features lawn games, picnic tables, Adirondack chairs, and fire pits. In the summer, stroll through the Path of Life Garden, a 14-acre outdoor sculpture park symbolizing life’s journey.

  • (2) Play a round of Golf at the John P Larkin Country Club, a scenic nine-hole semi-private golf course offering a relaxed and friendly atmosphere suitable for golfers of all skill levels. The course features a par-34 layout stretching 2,739 yards, with bent grass fairways and bluegrass greens, providing a challenging yet enjoyable experience (make sure you reserve a tee time).

  • (3) Embark on a river adventure with Great River Outfitters, offering canoeing, kayaking, and tubing along the Connecticut River (double check their website for advanced booking and departures times).

• 6:00 PM – 7:30 PM: Head back to downtown Windsor for a relaxing dinner at The Windsor Station Restaurant & Barroom offering a unique dining experience within a beautifully restored 1901 train depot, featuring locally sourced American cuisine, craft beers, and live music in a historic, railroad-themed setting. ​

• 7:30 PM – 10:00 PM: End the night at Georgetown Tavern, a lively bar and kitchen offering Indian and Caribbean-inspired cuisine, complemented by live music events in a welcoming atmosphere.

 

Day 2:

• 7:30 AM – 8:30 AM: Start the day with breakfast at Boston Dreams Café, a cozy café and sports-themed gallery offering freshly roasted Vermont coffee, paninis, bagels, and year-round ice cream.

• 9:00 AM – 12:00 PM: Head to Paradise Park (click here for PDF of trail map) for a morning hike and viewing the large patch of water lilies, fish or bird watch around Lake Runnemede where it's common to see our resident Bald Eagles.

• 12:00 PM – 1:00 PM: Re-fuel for lunch at Frazer’s Place, a beloved roadside diner serving classic American comfort food and infamous Maple Creemees during the summer season.

• 1:00 PM – 6:00 PM: Choose from the following:

  • (1) Explore our charming downtown at your leisure. Visit some of downtown Windsor's retail shops at Friends and Company, Sisters Weekend Marketplace, or Cassie's Resale Boutique. Or make an appointment ahead of time to pamper yourself at Tami's Headlines, Image Works Studios, Bob's Barber Shop or Points East Acupuncture. If your four-legged companion is along for the trip, choose from either the dog park at Railyards Recreation, a new addition to Windsor’s downtown that features pickle ball courts and a skate park, or take a short trip to Paradise Bark located at the Windsor fairgrounds.

  • (2) Visit the American Precision Museum, housed in the historic 1846 Robbins & Lawrence Armory, recognized as the birthplace of precision interchangeable parts manufacturing in the U.S. It features the nation's largest collection of historic machine tools and offers interactive exhibits that highlight the evolution of American manufacturing and its global impact.

  • (3) Visit Mount Ascutney State Park, which features a scenic 3.7-mile toll road that winds nearly to the summit, offering sweeping views and access to hiking trails. The road leads to a short hike to the 3,144-foot peak, making it a must-visit for nature lovers and history enthusiasts alike. Along the way, travelers can enjoy scenic vistas, picnic areas, and rest stops. For those interested in hiking, the park boasts over 12 miles of trails, including four routes that lead directly to the summit. Whether you choose to drive or hike, Mount Ascutney State Park provides a memorable experience with its rich history and stunning landscapes.

  • (4) Interested in hunting, fishing or birdwatching? The Windsor Grasslands Wildlife Management Area boasts 826 acres of woodlands, fields, and wetlands. The area is renowned for its diverse bird species, including nesting Northern Harriers and American Kestrels, making it a prime destination for nature enthusiasts. Windsor Grasslands is open to regulated hunting, fishing, and trapping in accordance with state laws and seasons. For detailed information on hunting and fishing regulations, seasons, and licensing in Vermont, visit the Vermont Fish and Wildlife Department. For more detailed information on birding, visit the Ascutney Mountain Audubon Society.

• 6:30 PM – 8:30 PM: For dinner, get takeout from Windsor Pizza Chef, Yummy Yummy Chinese, or Nadz Irie Jam.
  For finer dining and an evening drive, visit Skunk Hollow Tavern (Hartland), The Maple Kitchen (Brownsville), or The Common Man Restaurant (Claremont, NH), all located within close proximity (~15-20 minute drive) to downtown Windsor.

 

Day 2: Alternative Adventure Plan

From your previous day’s meal, you know that Windsor conveniently has an operating Amtrak station showcasing picturesque views of the Connecticut River. The Vermonter train* currently stops in Windsor at 11:56 AM (southbound) and at 5:56 PM (northbound). Try a visit to Brattleboro for its vibrant arts scene, eclectic downtown, and the perfect blend of small-town charm with progressive, creative energy (arriving in Brattleboro at 1:02 PM and departing back north at 4:56 PM).

* Please note: make sure you check the schedule for current operating times. The Vermonter currently stops only once a day going south and once a day going north and there is not an alternative pickup time or alternative transportation should you miss the scheduled train. (To complete a day trip you must travel south, if you go north you will need to secure overnight accommodations until the following day).

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Day 3:

• 8:00 AM – 9:00 AM: Have a leisurely breakfast at your lodging or a spot you might have missed the previous days: The Windsor Diner, Boston Dreams Café or Frazer’s Place.

• 9:00 AM – 9:30 AM: Visit the Cornish-Windsor Covered Bridge, built in 1866, is a historic wooden lattice truss bridge. At 449 feet in length, is the longest wooden bridge in the United States and the longest two-span, covered bridge in the world. It remains the longest wooden covered bridge still in use for vehicular traffic. Recognized as a National Historic Civil Engineering Landmark, the bridge exemplifies 19th-century American bridge-building craftsmanship and continues to serve as a functional and picturesque crossing between the twin states.

• 9:45 AM – 12:00 PM: Tour the Saint-Gaudens National Historical Park (just across the river in Cornish, NH), which preserves the home, studios, and gardens of renowned American sculptor Augustus Saint-Gaudens, offering inspiring art, beautiful gardens and walking trails, and scenic views of Mount Ascutney.

• 12:30 PM – 1:30 PM: Return to Windsor for lunch at a spot you might have missed the previous days: Windsor Pizza Chef, Yummy Yummy Chinese, Nadz Irie Jam, The Windsor Diner, Boston Dreams Café, or Frazer’s Place.

• 1:30 PM – 6:30 PM: Choose from the following:

  • (1) Visit nearby Ascutney Outdoors for hiking and trail running, mountain biking and equestrian trails during the summer months, or alpine skiing, snow tubing and cross-country & back-country skiing in the winter months.

  • (2) Get your lunch to go and drive to Kennedy Pond to swim and picnic. During the summer months, Kennedy Pond transforms into a cherished local swimming spot, featuring a small beach area and lifeguard supervision to ensure a safe and enjoyable experience for families and swimmers of all ages. This picturesque setting, surrounded by natural beauty, provides a perfect backdrop for swimming, canoeing, and kayaking, making it a favorite destination for both locals and visitors seeking a relaxing summer retreat.

  • (3) Or do one of the suggested previous day activities you might not have had time for!

• 7:00 PM: Depart Windsor, letting it's charm linger in your mind and spark thoughts of your next visit to this welcoming and historic town.