With apologies to Mitch Albom1
WILLIAMSBURG, VIRGINIA
This was my third ride in four weeks on this route. From a riding standpoint, there wasn’t much difference from the other ones. But, notable today, we had a presumed 82% tailwind. (Headwind was 18% so if it wasn’t a headwind, it must be a tailwind, right?)


Tim and I left Richmond Main and made our way to the Virginia Capital Trail. We followed the Cap Trail to Jamestown Settlement, went to the ferry loading area just to add a little distance, and then rode into Colonial Williamsburg.
Much like one of my favorite books, The Five People You Meet in Heaven (Albom), today it was Five People You Meet on a Ride. (I borrowed the title, and you should read his book.)


Person Number One
We came to the park in Henrico and met a man who was out enjoying the rare warm January day. It would reach 68° (20 °C). He started at Shockoe Bottom in Richmond and “was only” (his words) riding 20 miles as a 10-mile out-and-back. We told him our plans, riding to Williamsburg and taking the Amtrak back to Richmond. He didn’t know you could do that. The farthest he had ridden was Charles City and back, which was a 60-mile ride. I encouraged him to book a train and ride the entire route, because it would be the same 60 miles. He thanked us, and you could see him planning his next trip, which will be the entire route. He had said he wanted to do that but didn’t know how he would get back. Now he does.

Persons Number Two and Three
At Charles City, we stopped at Haupt’s Country Store. This had been my go-to stop for years. It is positioned halfway between Richmond and Williamsburg. The downside of this store is that there is no place to sit. Tim was running low on fuel and wanted to stop. We discussed possible lunch stops and decided to wait until Williamsburg and go for a burger from Retro’s in Williamsburg. I got shut out there on Christmas Eve when they were open only until 2:00 p.m., and I arrived at 2:30 p.m. We both agreed that lunch would be in Williamsburg.
At Haupt’s, two bikes were sitting outside. The riders, one named Henry, were inside. When they came out, we were asking them about their ride. When I saw they were headed back towards Richmond, I told them they would have a tailwind going back. They laughed. They knew.


They had ridden down to the Chickahominy River and were riding back. They knew it was a headwind. They laughed. We laughed. Henry asked, “How did you know my name?” I told him because it was displayed on my Wahoo.
Discussion turned to our ride, and, like the guy at Henrico, they never heard of the Amtrak option. I told them the key was to watch the weather and see where the prevailing winds were coming from. If coming out of the east, then take the 10:00 train from Richmond to Williamsburg and ride back. If the winds are out of the west, like they were today, then ride to Williamsburg and take the 4:00 train back to Richmond.*

We crossed the Chickahominy River and stopped on the bridge to admire the view. We had met three people on this ride, which, other than passing or being passed, is more than we normally meet. Aided by a tailwind, the ride was clicking by quickly. At Jamestown Settlement, we rode out to the ferry that crosses the James River to Scotland Wharf in Surry County. We discussed riding over and back, but it was much cooler down on the river, and we would not have much time for lunch before our 4:00 train. So we skipped the ferry.

Person Number Four
We continued on to Colonial Williamsburg. We made it to Retro’s, and as we arrived, Tim said that he was only 0.4 miles from a Metric (Metric Century or 62.14 miles). When I reminded him that we still had to ride to the train station, he replied with “What if something went wrong?” I laughed. Right in front of me was a young man who laughed. I looked at him and said, “Strava.” He replied, “I know, I’m a runner.”

Tim went around the block or two blocks to finish his Metric. I went to go inside Retro’s and saw a sign posted on the door. “Retro’s will close January 5th to 8th for maintenance.” Damn. My 2025 luck of finding closed attractions on my rides continued. I looked for the Wawa so we could eat something before we boarded the train. Tim came back, and I broke the news to him. When he suggested we go one street over, the guy I had been talking to said to go to Rick’s Cheesesteak Shops. I told Tim that my mantra is always to listen to a local, and he agreed. We went to Rick’s.
Before I left, I asked him if I could grab a photo for Strava. He laughed and said, “Sure.” And he added, “Be sure to tag me.” Well, I would if I could, but I don’t know his name.
Person Number Five
At the counter was a young lady whom I thought was probably a student at William and Mary. She was very pleasant and a joy to talk with. I found out she was a senior in high school and was facing the dreaded college decision. She was so very pleasant and just fun to talk with. After a long day in the saddle, it was an enjoyable way to finish. My day was made better because I talked with her.


In fact, my day was made better by talking to each of these Five People I Met on a Ride. Most rides are defined by the distance or the time, maybe even more so, the terrain or fixtures, such as bridges or tunnels. Scenery. Weather. So much enjoyment on a bike. But today, it came from the people.
Almost Person Six
At the train station, the station attendant came over, looked at me, and said, “I remember you.” What is this, Cheers, where everybody knows your name? It was nice, I think, being recognized, but he didn’t make the list. My day wasn’t necessarily made better by this interaction. This entry is The Five People You Meet on a Ride, not The Six People You Meet on a Ride.
EPILOGUE: The bike-train option is a great option. Our return train was 10 minutes late arriving, and then we were stopped for 20 minutes near Richmond after a vehicle struck a railroad bridge. Tim and I both asked to be left off the train to ride back. The conductor, the same jagoff who wanted to refuse me boarding in May, was not amused.
*Richmond has a Williamsburg train departing at 10:03 a.m. and 6:52 p.m. daily. Williamsburg has daily trains departing for Richmond at 4:24 a.m. and 4:07 p.m. This works best starting in Richmond unless one wants to start at 4:24 a.m. in Williamsburg. Weekend times are slightly different. i.e., the Richmond train for Williamsburg departs at 9:34 a.m.
If you are mentioned by name, reference, or photograph and wish for me to remove it, simply request that in the comments. Otherwise, thank you for making my day better.
Also, I have a photo of Person Number 5 that she granted permission for me to use for my Strava ride. But since she may have been a minor, I didn’t want to post it here. If she sees this and wants to give said permission, she can do so in comments by mentioning her school activity discussed, and the college she was applying to, where her brother also attends.
- Albom wrote the book The Five People You Meet in Heaven. (Highly recommended) ↩︎
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