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ShireCon 2026

It's the eighth year of our convention!


A two day convention for role-playing and board games in the Berkshires!


Come join us for a day-and-a-half of OSR and modern gaming, visit our vendors selling old and new games, and enjoy the local fare in North Canaan, CT.


Doors open at 12:00pm Friday and 8:00am Saturday. $35 pre-registration and entry to Friday and Saturday games, $20 at the door for each day (Friday, Saturday).

September 25-26, 2026

CT

06031

VFW Post 6851

Meet The Industry Guests

Each year, we invite several industry guests to ShireCon, to run games and hang out with attendees. Here is who is coming this year:

Erik Tenkar

Podcaster, OSR watchdog

Jeff Talanian

Hyperborea creator, author

Chet Minton

Artist, Author

Ian McGarty

Silver Bullette creator, author

Jayson Elliot

Tope Secret author

Joey Royale

Author

Levi Combs

Planet X, author

Todd Terwilliger

podcaster, author

Gaming Schedule

Friday,

 12:00pm

Guest Arrival

Guests can get their badges and set up for 1:00pm games.

Friday, 1:00pm

Game Block 1

Our first 4-hour block kicks off the convention!

Friday, 5:30pm

Game Block 2

Our second game block is 3 hours.

Friday, 10:00pm

Live Auction

Proceeds from the live auction go to the VFW! Get your bidding paddles at the registration desk before the event begins!

Saturday, 8:00am

Guest Arrival

Guests can register at 8:00am, get some breakfast or coffee at the VFW's food shack, and prepare for game block 3.

Saturday, 9:00am

Game Block 3

Our first game block on Saturday runs for 3 hours (until noon).

Saturday, 12:30pm

Giveaways and Writing Award

Tickets will get pulled for the free prize giveaways after we announce this year's writing award winner!

Saturday, 1:00pm

Game Block 4

Our second game block of the day is a 4 hour slot.

Saturday, 5:30pm

Game Block 5

Our last game block of the night is 3 hours.

Our Little Con

ShireCon draws about 150 guests each year, many who have been at every one over the last seven years. The convention takes place in rural CT in the foothills of the Berkshire mountains. Each year, Thom and his family organize and run this quaint, one-and-a-half day convention of games and fun.

ShireCon draws about 150 guests each year, many who have been at every one over the last seven years. The convention takes place in rural CT in the foothills of the Berkshire mountains. Each year, Thom and his family organize and run this quaint, one-and-a-half day convention of games and fun.

 

What Kind of Games Are Here?

Although all roleplaying and board games are welcome at ShireCon, many of the games found are old school style games (OSR), like AD&D, Shadowdark, Hyperborea, and Call of Cthluhu. Over the last few years, we've seen an increase in miniature war games too.

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Where Are We?

ShireCon is in North Canaan, CT 06018

Couch-Pipa VFW Post 6851

Est. 1947

104 S Canaan Rd. Canaan, CT 06018

(860) 824-8158

Food and beverages!

What Our Attendees Said

Attendees have expressed how much they enjoy coming to ShireCon - We'll let them share that with you in their own words.

M. Sherman, FL

Shirecon is an event I now look forward to attending every year! It is an awesome collection of gamers and creators that all come together to enjoy the roleplaying hobby. It is a smaller size con that really has a family gathering feeling. Great people, awesome games, its an event not to miss!

N. Green, NY

coming soon...

M. Roberts, MA

Coming soon...

FAQ

Fans of roleplaying and board games! ShireCon is an all ages show, so kids are very welcome too!

Most people attend ShireCon to play games. However, there are vendors to check out and other gamers to talk to. If you are staying in the area for a few days, the Appalachian Trail is nearby, plus other cool sights.

Yes! An outdoor food shack provides breakfast, lunch, and dinner with a variety of options. There are three bars on site too (for later in the evening).

Of course! We have youth and veteran badges.

North Canaan is a rural area but there are plenty of AirBnB's and hotels within 30 minutes (Great Barrington MA, north of the convention and Torrington, CT).

Don't Miss Out This Year!

Friday and Saturday in September

Wondering What ShireCon is Like?

Here is a video we made of the 2025 convention. Shot and directed by Yonah Sadeh.