The small town of Princeton, located in Worcester County, is a classic New England town that many people in Massachusetts don’t know much about, if they even know it exists. However, to the extent Princeton is ‘known’, it’s known for tennis. Princeton’s Labor Day Tennis Tournament, which was named the Chandler Bullock Memorial Labor Day Tennis Tournament in 1962 (while in its 50th year), is reported to be the oldest continually running private tennis tournament in the entire United States. The tournament is open only to current and former Princeton residents, their spouses, and their children who have reached the age of 15 by the start of the tournament each year. It may be small, but the skill level is high. SIGN UP FOR LABOR DAY TENNIS 2025 HERE!
As a realtor, the most common misconception that I hear as an objection about Princeton is ‘Nope, not Princeton. They don’t have the internet.’ I always burst with enthusiasm to say ‘YES WE DO, NOW!’ It’s almost embarrassing because I get so excited to tell people that as of 2019, thankfully before Covid, we now have high speed internet. They all laugh, and I’m totally serious.
Princeton is hidden in the forests and hills of Central Massachusetts, with a population just shy of 3,500 people, spread over 36 hilly and forested square miles. Much of the land in Princeton is protected by various land protection organizations such as the Princeton Land Trust, Mass Audubon and the Massachusetts Department of Conservation and Recreation, as well as various privately owned and protected tracts of land. It’s definitely rural; but it’s far from being a typical rural town.
Princeton is a beautiful place, with many homes dating to the colonial era, built mainly prior to the invention of air conditioning. There were people from Boston who had second homes in Princeton which, with an elevation of about 1,200 feet and a distinct and refreshing breeze, allowed them to escape the Boston summer heat. If you are a skier in Massachusetts or Rhode Island, you know Princeton, because of Wachusett Mountain State Reservation and Wachusett Mountain Ski Area.
Labor Day Tennis is a doubles tournament featuring men’s, women’s and mixed doubles. What makes this a particularly fun and unusual tournament, is that although the tournament is open to all people with the aforementioned Princeton connection, you don’t get to pick your own partner. The teams are formed by a random drawing, with the only tweaking being that players who have been finalists over the past three years will not be paired together. In addition, every effort is made to not pair players with the same partner going back three years, and immediate family members will not be paired together. There are typically about 100 players who sign up to play in the Labor Day Tennis Tournament, with late signups put on a waitlist. Match times, which are approximate, are updated on the Labor Day Tennis website. God bless the people who update the website during the tournament, as it’s the go-to source for exactly where you look to determine who you want to watch play, when and where, for the entire week of the tournament. SIGN UP FOR LABOR DAY TENNIS 2025 HERE!
Labor Day Tennis: Men’s, Women’s and Mixed Doubles
*Sign-ups are open now through 12:00 noon on Wednesday, August 20, 2025. Tournament play begins on Monday, August 25, and will continue through the week and throughout the holiday weekend, with finals played on Monday, September 2. Mixed Doubles will start on Monday, August 25. Men’s and Women’s Doubles will begin either Thursday, August 28, or Friday, August 29. —LaborDayTennis.com
Kids! Sign up for the Dan Hart Tournament!
This is a fun singles tournament open to Princeton kids who are under 15 years old by Labor Day. The dates for the tournament are August 21 through August 24, with some flexibility for players’ availability. Winners (1 boy and 1 girl) will be entered in the Labor Day Tournament. There will be a tune-up/practice session at Pine Hill Club for those interested. Send an email to danhart@publictennis.org to sign up. —LaborDayTennis.com
It’s been said that at one time Princeton had the most private tennis courts, per capita, in the US, but that’s pretty impossible now, or to even possibly figure out. In any case, Princeton has quite a few beautiful clay courts, available at two tennis/social clubs as well as a number of private courts scattered throughout town, many of which are open for use during the tournament. Incidentally, viewing the tournaments is open to anyone who wants to watch, particularly the finals.
All final matches are held at the Dan Hart Memorial Court at 5 Worcester Road in Princeton. Set your GPS to 5 Worcester Road and you’ll find yourself in the parking lot of the Prince of Peace Catholic Church in the center of town. It’s a beautiful location, with a view all the way to the Boston skyline in the background. It’s also an ideal spot for watching tennis, and features a huge downward sloping lawn, on which people spread blankets, set up chairs, bring picnics and enjoy a day of watching high level tennis. There is a referee who both calls the score and handles disputes, should any arise. Spectator attendance is usually 100+ people.
The vintage photo above shows a very young Terry Hart demonstrating his tennis skills alongside his father. Terry has given free lessons to youths on the Dan Hart Memorial Court every summer since 1986. Before him, his father gave the lessons at the Dan Hart Memorial Court, which was named after him. I maintain a page on my website dedicated to Princeton, which you can visit here to learn more about Princeton and Tennis in Princeton.
When we first moved to town, our daughter Erin, who was only 15 at the time, but had played tennis since she was very young, was matched up with Lee Digney, a seasoned Labor Day veteran player (and tournament champ). We felt bad for Lee, and were nervous because she had won the tournament multiple times over the years, and this year she was matched with a 15 year old. Over the course of days between when players knew who their partners were and the start of the tournament, Lee took Erin around to view potential competitors play, and gave her tips and formulated a winning strategy, basically imparting her tennis knowledge to our daughter.
They made it to the finals, after a number of close matches along the way, so that by the time they reached the finals, Jay was a nervous wreck….he could hardly watch, and I actually made a run home to get some beer for him at about 10am on Saturday–which, if you follow the tournament, you know that getting to Saturday afternoon is pretty cool, Sunday speaks to your level of play, and if you’re playing on Monday–you’re a top player in town (or at least matched up with one)! To our astonishment, Erin and Lee (shown hitting in the news video below) actually won. If you’re moving to a new town, and don’t really know many people, this is certainly a good way to get acquainted. That evening, the big post-tournament party was held in a large barn, so we had plenty to talk about.
Jay, who plays tennis, frequently participates, but has yet to get far enough in the tournament to make anyone nervous. I personally don’t play at all, but participate by coordinating the shirts and various Labor Day Tennis merchandise, which are a popular item during the tournament. Our son Adam and I design a different shirt each year, always with a different flair, so as to encourage people to buy this year’s shirt. I try to make them comfortable and attractive, but the main reason they sell is that people collect them. It’s fun to see various years’ shirts on the courts, and all proceeds go to Princeton Labor Day Committee, Inc., recently created as a non-profit 501(c)3 organization. In 2023, we added tumblers to the merch options. My car is the storefront, so when you see me at the tournament, you know that the shirts and tumblers are somewhere nearby. Payment can be made by cash, check or Venmo.
Want to know more about Princeton, perhaps considering a move here? Check out my About Princeton page!
