I am so tired from a week straight of tennis, and I don’t even play. The small town of Princeton, Massachusetts — you might miss it on a map, hosts the reputed oldest continuously running private annual tennis tournament in the country. And we’ve just wrapped up the 114th annual Chandler Bullock Labor Day Tennis tournament. This is a doubles tournament, with the options of signing up for men’s, women’s or mixed.
It’s truly difficult to describe what Labor Day Tennis means to people who participate in one way or another. To me, it’s magical. These are just my thoughts and others surely look at it differently — I’m just one spectator writing this, and with so many people involved, I know I’m not going to capture everyone, so please don’t take it personally if your role isn’t mentioned here. To some it might be just tennis, to many it’s competitive, to another group it’s social, and this year specifically I loved how many young children were at the matches and social events, growing up with this as a family tradition.
Labor Day Tennis typically starts the Monday before Labor Day, so eight days long. Because so many people signed up for mixed doubles this year, they actually needed to start a day early— so it went from Sunday, August 30 through Monday, September 7. If you’re curious about playing next year, don’t worry, you don’t need to take a week off from work. The weekday matches are typically played in the evenings. Once you get to the weekend, it’s just Tennis, Tennis, Tennis, with a lot of socializing and good conversation mixed in.
One of the things I love about Labor Day Tennis is that so many people play roles in and around the tournament. Like I said, I don’t play tennis — I don’t know how to score and I’m not even good at sweeping up the court. My role is designing, coordinating the production of, and selling the branded merchandise related to the tournament. All profits from my efforts are donated to the Princeton Labor Day committee, which is a 501(c)(3) non-profit.
There are seeded pairings of players, and those matchups don’t start playing on the first day. But the fun fact about the blind match of Labor Day Tennis players is that you could have signed up for your first time in the tournament, and been matched with Rusty or Tammy or Chris or Max. Forgive me for leaving out any crazy-good players in that short list, I’m just going from quick memory to create an understanding about the range in level of play. Fun fact about Chris that I learned at the trophy ceremony on Labor Day 2026 — for the past five years, Chris and his partner (a wide range of players) have made it to the finals in both men’s AND mixed.
Other very important roles, Kathy — who brings homemade blueberry muffins around on Saturday morning, the O’Briens, the Cronins and the Lilleys who generously offer their courts for tournament play. The Dan Hart Court at the Prince of Peace Church — only in Princeton would you find a Catholic Church with a beautiful tennis court and a view of Boston. The Pine Hill Club and Princeton Tennis Club, both facilities used heavily during the tournament. Then there’s the volunteers who make sure the Saturday luncheon is a success. And a new event this year, Heather and crew who were behind Rally On The Lawn, the Saturday night event with food trucks and live music and an unlimited s’mores fire pit. There were kids in raincoats–we weren’t letting a little rain spoil our fun.
We had crazy rainy weather some days this year and one evening during the earlier matches, we all had to cram into a small room at New England Tennis Center at Orchard Hills Athletic Club to watch 4 courts of indoor play as 40 people had to work through their matches.
At one point on Saturday, my daughter’s play was paused because of torrential downpours. The people manning the luncheon figured that’s where I was, and they were kind enough to pack up my merchandise to keep it safe from the weather. None of this runs itself, either — the Labor Day Tennis Committee puts in countless hours over the course of the whole year to pull this off–they kept the website updated every time weather forced a match or venue to change, which was the only reason any of us knew where we were supposed to be. Leading up to the finals, no Labor Day week would be complete without a fun potluck at Jess and Terry’s.
Then finals day — all day on Labor Day, at the Dan Hart Court at the Prince of Peace Church, the youth players of Terry Hart Tennis (free tennis lessons for kids each summer) with their hotdog stand, the trophy table, where people of all ages go to show others the names on the huge trophy. And then there’s the people who come up to my merchandise tent and are disappointed that I no longer have their size. On the 9th day of the tournament.
Some facts about Labor Day Tennis. You don’t need to live in Princeton to participate — you just need to have ever lived in Princeton. That’s why we see people coming from Florida, Utah and Washington, among other places outside of Princeton. Friends, and people who just like tennis join as spectators. There are people who have played in this tournament for 45+ years.
This 114th year of Labor Day Tennis actually saw 17 new players who signed up for the first time. That’s very exciting to me because it says this tournament is going strong. This year we celebrated one player’s 80th birthday–Happy Birthday, Pauline! And she wasn’t even the oldest player in the brackets. I believe that the highest age this year was 83, and there was a 16-year-old who advanced several rounds, along with her partner. Quite the age range.
Jay didn’t play this year, as he is scheduled for a knee replacement, not uncommon for tennis players. Our youngest daughter, Erin advanced a few rounds with both her mixed and women’s partners–Cindy for women’s and Alex for mixed. Alex was new to Labor Day this year–he married into the Lowenthal family, and turns out is an excellent player. In her women’s matches, they lost to Tammy and Lori, but when you get that far along in the tournament everyone is excellent, and someone has to lose. The level of play is impressive, and I think Erin just got out of it that she needs to play more often. Rumor has it that a couple of her siblings might consider going out next year, and my youngest three have been playing tennis together, so there’s a win right there.
This year saw some loss of Labor Day friends, and it was heartwarming to me to see people deep in conversation, comforting each other. We can’t predict what each year’s Labor Day Tennis tournament will look like, but we know it’s an amazing group of very welcoming people who come together to continue traditions and build onto it for the next generations.
Here’s a quick video I made. Want to see who won, browse photos from the week, or get the full history? Head to labordaytennis.com.
