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Vermont
Windsor County

Windsor

Attractions and Places To See around Windsor - Top 9

Best attractions and places to see around Windsor include a variety of natural and man-made landmarks. This region features prominent natural features like Mount Ascutney, offering elevated viewpoints and forested areas. The landscape also includes lakes and rivers, providing opportunities for scenic walks and exploration. Historic structures, such as covered bridges, contribute to the area's character.

Best attractions and places to see around Windsor

  • The most popular attractions is Observation Tower on Mount Ascutney, a man_made_monument that offers a…

Last updated: May 4, 2026

Observation Tower on Mount Ascutney

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Trails from all directions lead to the summit of Mount Ascutney. There's a lookout tower that takes you above the trees for great views.

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Little Cascade Falls

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Little Cascade Falls are a small set of cascades off the side of the Weathersfield Trail. They are often paired with the larger Crystal Cascade Falls at the end of the path.

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Cornish-Windsor Covered Bridge

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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New …

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A short skip and a jump from the summit/observation tower, this area provides a stunning view west over Vermont of Killington, Pico, and Okemo. You may also get lucky and …

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Lake Runnemede

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Lake Runnemede is a great place for a break during a long ride. The large body of water is home to many species of birds and fish. The water is …

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Popular around Windsor

Hiking around Windsor

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mtm05005
February 26, 2024, Lake Runnemede

Lake Runnemede is a great place for a break during a long ride. The large body of water is home to many species of birds and fish. The water is visible from the road, so if you don't have time to stop, you can still get a great view as you ride by.

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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New Hampshire and Vermont. Despite being nearly 160 years old, it still carries traffic every day. There is a pull-out here, where you can stop and take photos.

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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New Hampshire and Vermont. Despite being nearly 160 years old, it still carries traffic every day. There is a pull-out here, where you can stop and take photos.

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Grace Mulligan
December 22, 2023, Lake Runnemede

This is a lovely run around the shores of Lake Runnemede along a relatively flat and grassy footpath that's right up on the water's edge, creating lovely scenes as you make your way around.

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Matthew
November 29, 2023, Little Cascade Falls

Little Cascade Falls are a small set of cascades off the side of the Weathersfield Trail. They are often paired with the larger Crystal Cascade Falls at the end of the path.

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A short skip and a jump from the summit/observation tower, this area provides a stunning view west over Vermont of Killington, Pico, and Okemo. You may also get lucky and see some folks launching gliders. This is a must stop location if you happen to be up on Ascutney. Don't miss it!

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Mareike
December 20, 2022, Lake Runnemede

The shoreline of Lake Runnemede is a nice area for a walk. You can see Mount Ascutney in the background.

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Trails from all directions lead to the summit of Mount Ascutney. There's a lookout tower that takes you above the trees for great views.

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Frequently Asked Questions

What natural features can I explore around Windsor?

Windsor offers a variety of natural attractions. You can visit Lake Runnemede, a large body of water known for its bird and fish species, offering scenic walks along its shoreline with views of Mount Ascutney. For a more dramatic experience, explore Little Cascade Falls, a set of cascades located off the Weathersfield Trail. Beyond these, the broader Windsor Great Park provides ancient Royal landscapes with forests, grasslands, and lakes, ideal for enjoying the natural environment.

Are there any historical landmarks or sites to visit in the Windsor area?

Absolutely. Windsor is rich in history. A prominent historical landmark is the Cornish-Windsor Covered Bridge, built in 1866. It's the longest wooden covered bridge in the country, connecting New Hampshire and Vermont, and still carries traffic daily. Additionally, the region is home to the historically significant Runnymede and the Magna Carta Memorial, located just outside Windsor, where the Magna Carta was signed in 1215.

What outdoor activities can I do near Windsor's attractions?

The area around Windsor is perfect for outdoor enthusiasts. You can find numerous trails for various activities. For hiking, explore routes like Paradise Park Loop or the Windsor Trail. If you enjoy running, consider the Lake Runnemede 5k loop. Gravel biking is also popular, with options like the Gravel loop from Windsor. You can find more details and routes in the dedicated guides for Hiking around Windsor, Running Trails around Windsor, and Gravel biking around Windsor.

Are there family-friendly attractions in Windsor?

Yes, Windsor offers several family-friendly options. The Cornish-Windsor Covered Bridge is a fascinating historical site that families can enjoy crossing and photographing. Lake Runnemede provides a pleasant setting for family walks and observing wildlife. For a full day of fun, LEGOLAND Windsor Resort is a popular theme park with rides and interactive experiences suitable for all ages.

Where can I find the best views of the surrounding landscape?

For panoramic views, head to Observation Tower on Mount Ascutney, which offers a lookout tower above the trees. A short distance away, the West Peak Vista / Glider Area on Mt. Ascutney provides stunning westward views over Vermont, including Killington, Pico, and Okemo. You might even catch sight of gliders launching from this spot.

What are some unique cultural sites or experiences in Windsor?

Beyond the natural beauty, Windsor has cultural depth. You can visit Eton College, a renowned public school nearby, which offers tours and free museum access on Sunday afternoons. The Windsor Guildhall, designed by Sir Christopher Wren, houses the Windsor and Royal Borough Museum, providing insights into local history. For a unique local experience, consider a tour and tasting at the Windsor and Eton Brewery.

What is the best time to visit Windsor for outdoor activities?

While Windsor is enjoyable year-round, the spring and summer months (April to September) are generally ideal for outdoor activities like hiking, running, and exploring the parks and riverside. During these seasons, the weather is milder, and the natural landscapes, such as Pinkneys Green with its wildflowers, are at their most vibrant. Autumn also offers beautiful foliage, particularly in Windsor Great Park.

Are there any dog-friendly attractions or walks near Windsor?

Many of Windsor's outdoor spaces are dog-friendly. Windsor Great Park is an excellent choice for walks with your dog, offering vast open spaces and trails. The Long Walk, leading to Windsor Castle, is another popular spot for strolls. Always ensure dogs are kept on a lead where required and respect local signage regarding pet access.

What kind of walking trails are available around Windsor, and what are their difficulties?

Windsor offers a range of walking trails suitable for various fitness levels. You can find easy walks like the Paradise Park Loop or the Ridge and Lakeside Loop. Moderate trails include the Brownsville Trail and the Windsor Trail. For more challenging hikes, consider the Weathersfield Trail. Many trails, such as those around Mount Ascutney, lead to elevated viewpoints. For detailed information on distances and difficulty, refer to the Hiking around Windsor guide.

Can I find places to eat or drink near the attractions?

Yes, Windsor has numerous options for dining and refreshments. The town center, particularly near Windsor Castle and the River Thames, is dotted with historic pubs and cafes where you can enjoy traditional British fare and atmosphere. Many attractions, especially in Windsor Great Park, also have cafes or refreshment kiosks nearby. For a unique local experience, visit the Windsor and Eton Brewery for tours and beer tastings.

What are some unique experiences or 'hidden gems' in Windsor?

Beyond the main attractions, Windsor offers some unique experiences. Consider a Windsor Duck Tour for a distinctive perspective of the town and river from an amphibious vehicle. Exploring the numerous historic pubs provides a traditional British experience. For a sweet treat, visit the Windsor Fudge Kitchen or Chocolate Factory to see fudge being made and sample various flavors. The Savill Garden within Windsor Great Park is also a beautiful, diverse haven often overlooked by first-time visitors.

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Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

QuecheeWoodstock VillageWhite River JunctionWilderHartford VillageAscutneyNorth HartlandWest WoodstockNorwichSouth WoodstockHartland

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