The Route

This is a long, complicated ride with many variables (such as NY borough traffic) to consider. I've tried to incorporate a few variations to make this as approachable as possible!

In general, we do our best to prioritize more curvy roads (especially on Long Island) but doing this trip via curvy roads exclusively would extend this out into the 6-7+ hour territory. That's just not realistic considering you will want to park the bike at each castle for pics & to explore.

With that said, feel free to play with the map! The link below is fully editable and you can build your own variations.

Options

Here are a couple of options to consider:

1. The start of this trip assumes you are in Manhattan or close to it. If you would prefer to finish there instead, go ahead and start with Bannerman Castle up North instead and finish off in Central Park at Belvedere.

2. If traffic in the city is just too much to bare (especially if you're doing this on the weekend on a nice day), go ahead and skip Belvedere entirely. Pay attention to traffic on Long Island as well; it can get busy.

3. This entire trip can be cut down to 2 separate trips if you're short on time or would prefer to spend more time at each castle. If you're in Manhattan, start out at Belvedere, hit up Long Island, and finish at the Cloisters. There's a great cafe there or Oheka Castle for a mid-day lunch. Save the rest for another time or the following day.

4. There are a ton of great roads in the vicinity of Bannerman Castle & Castle by the Lake. If you're into more spirited rides with great twisties, consider riding around in the area (take a look at our Bear Mountain Twists guide for routes) and swing by Sloop Brewing for lunch & a drink.

Google Maps Links

Click on the Google Maps links below for a full waypoint by waypoint route

Become a paying subscriber of Premium to get access to this post and other subscriber-only content.

Already a paying subscriber? Sign In.

A subscription gets you:

• • Free $10 gift card from SA1NT to spend on the best damn riding gear
• • Waypoint links (Calimoto & GPX) for all routes
• • Long-form editorials & features
• • Easily accessible archive of past posts and features
• • Constantly updated lists of our favorite cafes, breweries, lunch spots, rider gear shops, dealers, and mechanics we trust