10 Thomas Point

March 2023

My work takes me to the DMV about once a month. I usually fly into DC, jump in a rental car, and head straight to the office in the Baltimore suburbs. Efficient. Predictable. Routine.

But this trip has special significance because I get to see Ryan.

He invites me to his home in Annapolis. We’re going to dinner that night, starting with a drink at his place. I’m following Google Maps to his address, enjoying the drive in a way I never have before — not because the roads are straightforward, but because anticipation makes me appreciate every turn more than the last.

Maryland was developed before urban planning was a thing. One drive will take you from shanty to mansion in the span of a single breath. It’s a patchwork of eras and incomes and architectural personalities, stitched together by winding roads and sudden water views. I’m curious about what I’m going to find — what kind of place Ryan calls home.

The road winds for a while, past subdivisions with identical mailboxes, then suddenly opens into stretches of multi‑acre homes with long driveways and old trees that look like they’ve been watching over the land for centuries. Then, without warning, the scenery shifts again — a flash of blue between the branches, a glimmer of sunlight on water.

A peek.

Then another.

Then, the full waterfront on both sides, like the road has decided to show off.

It’s beautiful in that understated, East Coast way — not dramatic, not loud, but quietly confident. The kind of beauty that doesn’t need to announce itself. Hey, there is a waterfront view over here!

Ryan and his ex‑wife bought this home on Fishing Creek. After a flood, it was finally financially possible to have such an amazing property — if he was willing to put in the sweat equity. And he was. He spent years rehabilitating the home, restoring it piece by piece, until it became something worth showing off. They found a single woman to rent the main house, and another renter above the garage. When his divorce left him homeless, he moved into the in‑law apartment above the garage.

What a nice location to have on reserve for a bachelor pad.

The apartment sits high enough to catch the light, with panoramic water views — the kind of views that make you pause mid‑sentence. A brief walk takes you to Thomas Point Park, where the lighthouse stands like a watercolor brought to life.

I park the car and step out, taking in the quiet, clinking sound of sails in the distance. It’s peaceful. Unexpectedly peaceful. The kind of place that slows your breath.

I think I like Annapolis.

And maybe — just maybe — I’m starting to understand why Ryan loves it here.