Pine Tree Associates

Pine Tree Associates is tucked away in a quiet, wooded area just outside Annapolis, and once you’re close, it’s surprisingly straightforward to find. That said, it does feel a bit hidden - which is kind of the point. Expect a short drive down country-style roads before you reach the entrance, where things quickly shift from suburban Maryland to a more secluded, back-to-nature vibe.

By Car:
Driving is by far the easiest way to get here. From Annapolis, it’s about a 20–25 minute drive, while from Baltimore or Washington, D.C., you’re looking at roughly 45–60 minutes depending on traffic. You’ll head toward the Crownsville area and then onto Hawkins Road, where signage for Pine Tree is modest but visible if you’re paying attention.
Parking is available on-site, and once you arrive, you’ll check in before heading into the grounds. It’s worth noting that this is a private club, so you should arrange your visit in advance rather than just showing up.

By Public Transport:
Public transport isn’t really practical for Pine Tree. There are buses that get you partway toward Crownsville from Annapolis or Baltimore, but you’d still be left with a long walk or needing a taxi or rideshare to cover the final stretch.
If you’re not driving, your best bet is to combine transit with an Uber or Lyft for the last leg - but overall, having your own car will make the experience much smoother.