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Highwood

Top 4 Castles around Highwood

Best castles around Highwood include a variety of historical sites and castle-like structures. While traditional medieval castles are not present in Highwood, the area offers unique properties and nearby attractions with architectural grandeur. These include purpose-built castles a short distance away and elaborate mansions. The region provides opportunities to explore historical architecture and significant estates.

Best castles around Highwood

  • The most popular castles is Chipping Ongar Castle, a settlement that was once the centre of an Anglo-Saxon hundred. Although…

Last updated: June 29, 2026

Chipping Ongar Castle

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Chipping Ongar is a pretty market town with a rich history. It was once the centre of an Anglo-Saxon hundred, an administrative area developed during the period. In 1162, Richard …

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Pleshey Castle was completed around the turn of the 12th century and was a motte and bailey. These days, nothing much survives, apart from the earthworks, sections of mote, and …

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No remains of the castle exists, but still nice to walk around and explore.

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Remains of the Norman Castle Mound

Highlight • Historical Site

An amazing place, not too much to see, brilliant view from the top, have a guided tour to understand why it was here and what it was like back in the day.

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Pleshey Village

Highlight • Settlement

Quaint village, site of a former royal castle, now just the earthworks left (sadly mostly obscured from view and on private property).

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George
December 12, 2025, Remains of the Norman Castle Mound

An amazing place, not too much to see, brilliant view from the top, have a guided tour to understand why it was here and what it was like back in the day.

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Dirty Wknd
November 8, 2022, Pleshey Village

Pretty Essex village centred around the village pond. A lovely spot to stop for a breather or refreshment.

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Quaint village, site of a former royal castle, now just the earthworks left (sadly mostly obscured from view and on private property).

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No structure of the castle remains and are located on private land, but you can still see the high mound of the Norman motte and bailey. And Ongar has some lovely shops and eateries.

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Beautiful village of chipping Ongar With great walks and the oldest wooden church in the world.

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Pleshey Castle was completed around the turn of the 12th century and was a motte and bailey. These days, nothing much survives, apart from the earthworks, sections of mote, and a 14th-century brick-built bridge. You still get a good sense of the fortification, though.

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Chipping Ongar is a pretty market town with a rich history. It was once the centre of an Anglo-Saxon hundred, an administrative area developed during the period. In 1162, Richard de Lucy, Chief Justice of England, built a great castle in the town. Whilst the castle was demolished in the 16th century, you can still see the site. You find some decent pubs and restaurants in the town, making it a good choice for a pit-stop. There is also a vintage railway line.

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No remains of the castle exists, but still nice to walk around and explore.

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Frequently Asked Questions

What kind of 'castles' can I expect to find around Highwood, Illinois?

While Highwood, Illinois, doesn't have traditional medieval castles, the area offers unique properties that evoke a castle-like grandeur. You can find a genuine, purpose-built gothic castle a short distance away, as well as impressive residences and mansions with notable architectural styles that are often available for events or luxury stays.

Where can I find a true castle experience near Highwood?

For a true castle experience, you should visit Bettendorf Castle in Fox River Grove, a neighboring community. This unique gothic castle features towers, turrets, a water-filled moat, a working drawbridge, and a dungeon. It's available for tours, events, and photo shoots, offering a fascinating destination for history buffs and families. You can learn more about it at Castlesy.com or Visit Lake County.

Are there any historical mansions or grand estates to explore in the Highwood area?

Yes, Highwood and its affluent North Shore communities feature many large, architecturally significant homes that offer a sense of grandeur. These include properties like a 1930s era original mansion with a southwest stucco design, or a secluded mansion in Riverwoods. The Fort Sheridan Captain's Mansion in nearby Highland Park, built in 1890, also offers a glimpse into historical luxury architecture with its period details and Lake Michigan views.

What activities are available at Bettendorf Castle?

Bettendorf Castle offers a variety of activities including tours, weddings, photo shoots, and various public and kid-friendly events. Its unique history and authentic medieval design elements make it a captivating destination. It has also been used as a honeymoon suite and for filming commercials.

Are there family-friendly options among the castles or castle-like attractions?

Yes, Bettendorf Castle is known for its kid-friendly events and offers a whimsical experience for families. While the grand mansions are primarily event venues, their unique architecture can be appreciated by older children interested in design or history.

What kind of architectural styles can I see in the grand homes around Highwood?

The grand homes and mansions in and around Highwood feature diverse architectural styles. You might encounter unique designs like Southwest stucco, Tudor-style homes from the 1920s, or classic 1930s mansions with ornate fixtures. The Fort Sheridan Captain's Mansion, for example, showcases high-end millwork and finishes typical of late 19th-century luxury.

Can I find walking routes or outdoor activities near these castle-like properties?

While specific walking routes directly to the castle-like properties might vary, the Highwood area offers numerous outdoor activities. You can find various hiking routes, such as the easy 'Deer Herds loop from Highwood' or the 'The Cricketers loop from Highwood'. For more options, explore the Hiking around Highwood guide.

Are there cycling opportunities near the Highwood area's attractions?

Yes, the region around Highwood provides excellent opportunities for cycling. You can find gravel biking routes like the 'Pleshey Rolling Hills – Pleshey Village loop' or mountain biking trails. Check out the Gravel biking around Highwood guide or the MTB Trails around Highwood guide for detailed routes.

What historical context does the Fort Sheridan Captain's Mansion offer?

The Fort Sheridan Captain's Mansion, built in 1890, offers a glimpse into historical luxury architecture and is part of the Fort Sheridan area. This area is recognized for its interesting history, architecture, and nature trails, providing a rich historical context to the region and appealing to those interested in opulent, well-preserved estates.

What are some unique features of the grand mansions in Highwood?

These grand mansions often feature unique architectural styles, spacious interiors with high ceilings, grand staircases, elegant fixtures, and expansive grounds. They provide luxurious settings suitable for events, photo shoots, or filming locations, offering a lavish backdrop for special occasions.

Are there any hidden gems among the castle-like sites near Highwood?

Bettendorf Castle, with its dedicated craftsmanship and authentic medieval design elements, can be considered a hidden gem for those seeking a unique historical and fantastical experience in the region. Its detailed features like a working drawbridge and dungeon are quite rare for the area.

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Looking for the best castles somewhere else? Discover other guides around Highwood:

RoxwellPlesheyGreat And Little LeighsGreat WalthamWrittle

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