Category Archives: Sports

Caption this photo

Please share a caption of your own for this week’s photograph. Hopefully the caption I’ve shared below will inspire you to leave a funny caption in the comment section. If you don’t see it immediately, don’t worry, I’ll approve it for readers to enjoy.

When you gotta go, you gotta go

Provincetown Film Festival fundraiser

Will you be in Provincetown Saturday, May 20th? Check out the Provincetown Film Festival Society’s first annual Pickleball Tournament to benefit the 25th Anniversary of the popular film festival. You can learn more about this year’s film festival and the Pickleball Tournament (including how to register to participate) by visiting

Red Bull Cliff Diving World Series returns to Boston this June

The Red Bull Cliff Diving World Series will come to Boston next month on Saturday, June 3, 2023. This annual tour first came to Boston in 2011 and this will mark the fifth time the competition has brough some of the world’s best cliff divers to the city. The backdrop of Boston’s skyline and harbor makes for some impressive photos and draws huge crowds to the Seaport each year.

Boston lacks cliffs (we barely even have hills) so Red Bull turns the Institute of Contemporary Art into a 90′ diving platform. If you’ve never been, mark this date on your calendar and check it out. The best views are from Pier 4, but the largest crowds will congregate on Fan Pier.

Below is a video I created after going to the first competition in 2011.

2011 Red Bull Cliff Diving World Series in Boston

Caption this photo

Hopefully the caption I’ve shared below inspires you to offer up one or two of your own. Leave a funny caption in the comment section, and I’ll approve it for readers to enjoy.

Potty Humor

Boston Pride Hockey’s Thursday night skating returns

Boston Pride Hockey’s “Pick-Up Pass” is back this winter for all of you who like to skate. The pass allows you to skate through April 6th at the Simoni Skating Rink in Cambridge each Thursday night.

This is a great way to get out, meet people and be more active during the winter months. For more information about Boston Pride Hockey and their annual winter skating at Simoni Skating Rink in Cambridge visit,

Caption this photo

This weekly post would hardly last a month if it weren’t for the many odd and awkward sporting photos that have been contributed over the years. Much thanks to Mike from NY for sharing this week’s photo.

Hopefully the caption I’ve shared below inspires you to offer up one or two of your own. Leave a funny caption in the comment section, and I’ll approve it for readers to enjoy.

Here, let me get this for you. That’s much better.

The Big Gay Donation: FIFA edition

Much thanks to Fearsome Beard for sharing this a few days ago. And much thanks to Miriam Margoyles for putting this together. In her educational video, Miriam points out that, luckily the wonderful upstanding people who run Football [FIFA WORLD CUP] love “donations”.

Give this clip two minutes of your time.

The 2023 Bob-Spread Calendar

Last year’s innaugural Bob-Spread Calendar was realeased ahead of the 2022 Winter Olympics. The eye-catching pg-13 rated photos were definitely popular, and I made the case that the proceeds from sales which supported the men on the US bobsled team was just icing on the cake for making this purchase. The photos are being included in a new 2023 calendar that is for sale.

The models (and members of the 2022 US Men’s Bob Sled Team) include team: drivers – Hunter Church and Codie Bascue, and push athletes – Hakeem Abdul-Saboor, Kris Horn, Blaine McConnell, Jimmy Reed, Nic Taylor, Carlo Valdes, Charlie Volker and Josh Williamson.

Orders placed by Wednesday, December 21st will arrive in time for Christmas and make for a great gift or Yankee Swap at $25.00.

2023 Bob-Spread Calendar

Winter Rendezvous: Gay ski week at Stowe Mountain

Winter Rendezvous is New England’s largest and longest running gay ski week party. This year the event will take place January 18-22, 2023. For those of you trying to buy a holiday gift for someone who enjoys skiing, this may be the perfect present. Winter Rendezvous includes events each night at the gorgeous Stowe Mountain resort in Vermont.

Official lodging venues include Top Notch Resort (host hotel), Brass Lantern Inn, and Stowe Motel, but people will be making reservations wherever they can find space and if you’re thinking of going, I’d recommend you do the same before places sell out.

This year’s parties and entertainers will include an amazing Tina Turner tribute by Debby Holiday, Miss Richfield 1981, Miss Jackie Beat, and several dance parties with great DJs. For more information about Winter Rendezvous 2023 visit the website,

Caption this photo

Initially I thought this clip was hilarious but then I started thinking, I wonder what readers of BosGuy might have to say, and I decided it would make for a great caption this photo (or in this case, clip) post. Would love to read some witty captions.

Boston Pride Hockey presents The Frozen Unicorn 2023

Registration for The Frozen Unicorn 2023 is now open.

Boston Pride Hockey is excited to announce New England’s LGBTQ+ 2nd annual pond hockey tournament will take place January 20 – 22, 2023 at Lake Morey Resort in Fairlee, Vermont. This year’s outdoor hockey tournament will expand and include players from beyond New England to include players from across the United States and Canada.

All skill levels are welcome to participate in the tournament. A draft party will be held at 8pm on Friday January 20th, and games will begin the morning of Saturday, January 21st at 8am, concluding 3pm on Sunday, January 22nd.

For more information about registration, logistics and additional events planned for the tournament are available on the event website,

Head of the Charles Regatta


The Head Of The Charles Regatta (HOCR) is a Boston area tradition that dates back to 1965 and has evolved into a massive, international rowing competition that draws nearly 11,000 athletes and 400,000 spectators, making it the largest rowing event in the world.


The 2022 HOCR takes place this Saturday and Sunday. Sadly, I’ll be out of town and will miss this fun, annual event. If you’ve not been to this premiere rowing events, head down to the Charles River to cheer on these amazing athletes and enjoy all the activity around the regatta.

The organizers have created a great website that includes more information about the races, maps and FAQs. You can learn more by visiting the official HOCR website,

Caption this photo

Hopefully the caption I’ve shared below inspires you to offer up one or two of your own. Leave a funny caption in the comment section, and I’ll approve it for readers to enjoy.

“Your hands can’t touch the ball!”

25th Annual Ptown Soccer Classic is next month

The 25th Annual Provincetown Soccer Classic that will take place over Indigenous People’s Day Weekend in Provincetown (formerly known as Columbus Day Weekend). The Strikers’ annual Provincetown soccer classic is a social and welcoming soccer tournament for all skill levels, promoting and celebrating LGBT sports and in particular soccer.

The weekend’s tournament events this year will include the Welcome Party, Wigs & Heels Tea Dance, a full day of soccer, Dinner Banquet, and more. Below is a tentative calendar of events.

Friday, October 7

8pm – 11pm: Opening Party @ The Underground Bar 293 Commercial St
11pm: Late Night @ A-House 6 Masonic Place 

Saturday, October 8

12pm – 2pm: Waterfront Cocktails and Gossip @ Harbor Lounge 359 Commercial St 
4pm – 7pm: Wigs & Heels Tea Dance @ Boatslip 161 Commercial St
9pm – 11pm: Post-Dance Party @ Wave Bar 247 Commercial St
11pm: Late Night @ A-House 6 Masonic Place 

Sunday, October 9

8am – 8:30am: Soccer Registration @ Motta Field 25 Winslow St
9am – 3pm: Ptown Classic XXV Tournament @ Motta Field 25 Winslow St
5pm – 8pm: Closing Banquet @ The Club 
8pm – 11pm: Post-Tourney Party @ The Shipwreck Lounge 10 Carver St p
11pm: Late Night @ A-House 6 Masonic Place 

Monday, October 10 – See you next year!

Click here for more information

Caption this photo

Hopefully the caption I’ve shared below inspires you to offer up one or two of your own. Leave a funny caption in the comment section, and I’ll approve it for readers to enjoy.

“So you’re telling me this is a popular sport played by heterosexual men?”