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Castle Island

The best cycling routes around Castle Island

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106

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24

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Touring cycling around Castle Island, a 22-acre peninsula in Boston, Massachusetts, features scenic coastal paths and paved pathways. The area offers panoramic views of Boston Harbor and the Boston Harbor Islands. The shoreline includes parks and beaches, complemented by green grassy lawns and shaded picnic areas.

Best touring cycling routes around Castle Island

  • The most popular touring cycling route is Delamont to Ardglass Harbour loop, a 32.1 miles (51.7 km) trail that takes 3 hours 5 minutes to complete. This route features moderate elevation changes.
  • Another top favourite among local touring cyclists is Saint John's Point loop from Downpatrick — Strangford & Lecale, a moderate 39.0 miles (62.8 km) path. It offers varied terrain with notable elevation gain.
  • Local touring cyclists also love the Saul to St Patrick's Well loop, a 21.2 miles (34.1 km) trail leading through diverse landscapes, often completed in about 2 hours 2 minutes.
  • Touring cycling around Castle Island is defined by coastal paths, harbor views, and paved pathways. The network offers options for different ability levels, from easy loops to more challenging routes.
  • The routes in Castle Island are highly rated by the komoot community with an average score of 5.0 stars from over 4 reviews. More than 174 touring cyclists have used komoot to explore Castle Island's varied terrain.

Last updated: May 15, 2026

4

riders

#1.

Kilclief to Ardglass Harbour loop —Strangford & Lecale

29.2km

01:46

150m

150m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

4

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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

Beyond the Horizon
November 1, 2024, Lough Money

Lough Money is a quiet, almost mystical place, perfect for relaxing and taking a deep breath. The gentle waves of the lake gently hit the shore, while the reeds sway in the wind, creating a gentle rustling sound. Surrounded by rolling countryside and shady trees, you feel like you've been transported to another world. Ideal for a break on your bike ride.

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The vast coastline stretches out endlessly before you, and the panorama with the majestic Mourne Hills in the background creates a scene that is hard to put into words. The gentle waves touching the sand and the silence of the surroundings make you feel the vastness and freedom of this place.

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This impressive stone circle, dating from the late Neolithic to early Bronze Age, consists of over 50 upright stones enclosing a diameter of around 35 metres. Access is via a narrow hedge-lined path that takes you directly to the entrance of the circle

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One of the best kept Circles I know of. The late Neolithic to earlier Bronze Age monument was excavated in 1937–1939 but its development and date are still not entirely clear. Excavation uncovered a slab feature with three compartments at the west end of the cairn, which could suggest the court tomb tradition, and a single stone cist at the east end which could point to the passage tomb tradition. Cremated remains representing at least seven individuals and some Neolithic pottery were found. Parallels for the outer stone circle with sites in Cumbria have been suggested.

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sm milligan
November 25, 2023, St Patrick's Well

The Well is an ancient site of pilgrimage with legends of Saint Patrick. The waters of the well are said to cure any ailment. Saint Patrick founded Ardtole Church which can be seen on the horizon. In the next field at low tide Saint Patrick's Road becomes visible. This was to be his route to the Isle of Man but when a red haired woman crossed his path he seen it as a bad omen and didn't make the journey.

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sm milligan
November 25, 2023, Lough Money

Lough Money is the source for the River Slaney, which flows to the supposed landing spot of Saint Patrick on Strangford Lough. Lough Money’s water is remarkably clear as befits a facility that was once used as a reservoir for Downpatrick. The remains of the disused pumping station still stand on the island. Beautified by the presence of herons, just one of many bird species that comprise an abundance of bird life.

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Windmill Hill is steeped in history. The remains of a windmill at the top of the hill are a reminder of a bygone era. Built in the late 1700s, the mill was used to grind wheat for the production of flour. But the picturesque site has also witnessed turbulent times and holds memories of the Battle of Ballynahinch. The battle, on June 12, was part of the 1798 Irish Rebellion fought between British forces and the United Irishmen.

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sm milligan
November 24, 2023, Annadorn Dolmen

The Dolmen can be found on the north east shore of Loughinisland Lake, within sight of Loughinisland Church. A slightly displaced capstone covers a rectangular chamber of which three side stones survive. An early account suggests that this was formerly inside a large circular cairn and approached through a lintelled passage, so it may be the remains of a passage tomb. It is famous as the platform from which Thomas Russell addressed a crowd of United Irishmen in 1803, after the main 1798 rising.

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Frequently Asked Questions

How many touring cycling routes are available around Castle Island?

There are 25 touring cycling routes around Castle Island, offering a variety of options for different skill levels. This includes 6 easy routes, 16 moderate routes, and 3 more challenging paths.

What kind of terrain can I expect on the touring cycling routes around Castle Island?

The touring cycling routes around Castle Island primarily feature paved pathways, making them smooth and accessible. You'll enjoy scenic coastal paths with refreshing breezes and picturesque harbor views.

Are there any easy touring cycling routes suitable for beginners or families?

Yes, Castle Island offers 6 easy touring cycling routes. A great option for a relaxed ride is the Mallard Plantation – View of Castle Ward Mansion loop from Portloughan, which is 9.1 miles (14.7 km) long and features minimal elevation gain.

What are some of the main attractions or landmarks I can see while cycling around Castle Island?

While cycling, you can explore several historical and natural attractions. The most prominent is Fort Independence, a massive five-pointed granite structure. Other points of interest include a monument to Donald McKay, the builder of famous clipper ships, and a fishing pier. For more details, you can explore attractions like Castle Ward Tower or Audley's Castle.

Are there any specific areas where cycling is restricted on Castle Island?

Yes, cyclists should be aware that bike riding is prohibited directly around Fort Independence and on the Causeway. In these specific areas, riders are required to dismount and walk their bikes to ensure the safety of all park-goers.

What is the best time of year to go touring cycling in Castle Island?

Castle Island offers pleasant cycling conditions for much of the year. The spring and fall often provide comfortable temperatures and fewer crowds. Summer is also popular, though it can be warmer, and the area benefits from refreshing sea breezes.

How can I get to Castle Island using public transport?

Castle Island is accessible via Boston's public transport system, the MBTA. Specific bus routes serve the area, and you can plan your journey using the MBTA's official website for the most current schedules and connections.

Where can I park my car if I'm bringing my own bike?

There are parking options available near Castle Island. While specific fees may apply depending on the time of year or day, there are designated parking areas for visitors. You might also find parking at Castle Ward Shore Car Park.

Are there any circular touring cycling routes around Castle Island?

Yes, the most notable circular route for cyclists is the Pleasure Bay Loop, which extends just over two miles around the island and Pleasure Bay. This loop is known for its refreshing breezes and picturesque harbor views.

What do other touring cyclists say about the routes in Castle Island?

The touring cycling routes in Castle Island are highly rated by the komoot community, with an average score of 5.0 stars from over 4 reviews. Cyclists often praise the scenic coastal paths, harbor views, and the well-maintained paved pathways.

Are there options for renting bikes near Castle Island?

Yes, for those without their own bikes, Boston's Blue Bikes bike-sharing program has stations conveniently located near Castle Island, allowing visitors to easily rent and return bicycles for their ride.

What are some longer, more challenging touring cycling routes in the area?

For those seeking a longer and more challenging ride, consider the Saint John's Point loop from Downpatrick — Strangford & Lecale. This moderate 39.0 miles (62.8 km) path offers varied terrain with notable elevation gain, providing a more demanding experience.

Are there any places to eat or drink near the cycling routes on Castle Island?

Yes, Castle Island features Sullivan's, a popular seasonal snack bar serving classic seaside fare. Additionally, the surrounding Boston area offers a wide array of restaurants, cafes, and pubs for post-ride refreshments.

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