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. To the extent Princeton is ‘known’, one of the things 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 2026 HERE! And if you’re curious to see who is already signed up, you can find that list 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 2026 HERE!
Labor Day Tennis: Men’s, Women’s and Mixed Doubles
*Sign-ups are open now through 12:00 noon on Wednesday, August 26, 2025. Tournament play begins on Monday, August 31, and will continue through the week and throughout the holiday weekend, with finals played on Monday, September 7. Full details below and also at LaborDayTennis.com
Kids! Sign up for the Dan Hart Tournament!
This is a fun singles tournament open to current or former Princeton residents who will be 14 or younger as of August 31, 2026. This is a singles tournament, and is always a lot of fun. There will be a boys draw and a girls draw, and the winner of each will be eligible to play 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 are shown warming up and playing in the YouTube News video below.
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.
What do I have for Labor Day Tennis merchandise this year? 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., a non-profit 501(c)3 organization.
Since 2023, I’ve been adding other merchandise–like tumblers, seat cushions and to the merch options. My car is the storefront, so when you see me at the tournament, you know that the shirts and additional merchandise are somewhere nearby. Payment can be made by cash, check or Venmo. For 2026 I have the traditional t-shirts in adult and kids sizes, a ladies tank option, adult long sleeved lightweight hoodie, ladies full zip lightweight hoodie, pint glasses, trucker hats and more! I’ll be set up at Princeton’s Block Party at The Thirsty Lab on Sunday, August 29–watch for an email with merchandise details to pre-order or stop in at the Block Party to browse the merchandise and get yours before supplies run out!
The tournament has local sponsors–you can find out more here as to how to show your support for the tournament.
Want to know more about the food and social events? Check back here as the tournament approaches.
From LaborDayTennis.com
Here are the pertinent dates for this year’s tournament so you can all mark your calendars and make your plans:
- Sign-ups open Wednesday, August 5, 2026 at 8AM
- Sign-ups close Wednesday, August 26 at noon
- Wait-list sign-ups open Wednesday, August 26 at noon
- Draws posted Friday, August 28
- Mixed matches start on Monday, August 31 at 6PM
- Men’s and Women’s matches start either Thursday, September 3 or Friday, September 4, depending on the size of the draws
- All weeknight match schedules start at 6PM, with later matches scheduled as needed
- Finals will be held on Labor Day, Monday September 7, starting at 10AM
The eligibility rules for signing up are:
- You must be a current or former Princeton resident, or the spouse of a current or former resident
- You must be at least 15 years of age by the beginning of the tournament
- You must be available to play at all potential match times for the event(s) you sign up for, up to and including finals day – you never know who your partner(s) will be!
- Mixed: Monday (8/31) – Friday (9/4) evenings 6PM on, Saturday (9/5) – Sunday (9/6) 9AM – 5PM, Monday (9/7) 10AM – 4PM
- Men’s and Women’s: Thursday (9/3) – Friday (9/4) evenings 6PM on, Saturday (9/5) – Sunday (9/6) 9AM – 5PM, Monday (9/7) 10AM – 4PM
Note that the winners of the Dan Hart Tournament for kids up to age 14 (one girl and one boy) will be entered into the Labor Day Tournament if they wish to participate. This is the only exception to the age rule.
Want to know more about Princeton, perhaps considering a move here? Check out my About Princeton page!
