In 2010 I went to my first Keystone Conference, as Karen before I transition full time. When I was invited by a friend to go to this conference, I was so excited to be able to meet old friends and make new ones for life. After seeing a few friends, I checked in with the hotel’s registration desk, and to my surprise I was welcomed with smiles by a wonderful staff. I then checked in with the conference registration table for my name tag and program book. A book full of information on workshops schedules, from life stories to Gender Confirmation Surgery.

As I walked through the vendor’s room, I picked up a lot of information of programs on support groups, upcoming events, clothing, jewelry, photos, makeup artist, doctors, name change, etc.

Later I went to change into my bathing suit to get in the jacuzzi. While in the jacuzzi I met up with some friends to talk about what workshops we might attend. Having great conversations with old friends and new ones, about where they were in their journey.

One of the nicest things at the conference is meeting up with my sorority sisters with the Vanity Club. We all get together for drinks and diner as a group, and then we have an induction and pinning new ladies to the group. I do not know why, but some people think that the Vanity Club are snobs. Maybe it is because there is a cap on how women we will have in our group. You also need to be recommended by someone in the group and later be voted in. The cap to the group is 500 ladies and it is only Transgender ladies can be in the group.

There is a restaurant called the Dog & Pony, that serves good drinks, breakfast, lunch, and diner. Here is a chance to meet new ladies coming out for the first time, and making them feel comfortable with encouragement in who they are. Introducing them to my friends and vendors that may be able to help them with fashion, make up and clothes. No one will make you feel out of place, only to encourage the woman inside of you. One lady who is awesome with makeup is Elizabeth Taylor with Makeovers with Elizabeth Taylor. Her make up on you will make you look so beautiful and you will not even recognize yourself.

Workshops are about Coming Out to Family and Work, Law, Safety, and Surgery for Transwomen and Transmen. You hear Transgender speakers about their struggles or positive uplifting stories. What made their transition go well or the mistakes that were made. You get to hear and see how to walk and talk like a woman. They have keynote speakers who come in and speak to the group for lunch and dinner to motivate us.

The greatest thing about the Keystone Conference is the Dinner Dance Gala, where you will see awesome gowns being worn. Before we all go into dinner, there is cocktails, and photos taken by Cassandra Storm Photography, Inc. Cassandra takes the most beautiful photos, that bringing out the true beauty in you. During dinner, the food is awesome and filling with wonderful conversation. After dinner we hear from a keynote speaker and then a fantastic all-girl band to dance too called Wicked Jezabel, playing all kinds of music.

The greatest thing I want to say about being at Keystone is being treated by the staff at the Sheraton Hotel Harrisburg PA., with total respect. Their staff over the years love us to death. A lot of the staff have told me that a lot of the staff looks for us each year, and they request to sign up to work. A lot of the staff even remember who we are from past years. I just love the Keystone Conference for a lifetime experience!

You can find me at or visit my personal website at In my next article I’ll talk about “Love Before and After Transition”. Until then Shoot for the Moon and even if You Miss, You’ll Be Among the STARS!

Author Profile

Karen Kendra Holmes
Karen Kendra Holmes
Karen Kendra Holmes works for the Federal Government as a Safety Officer. Besides her full- time job with the Federal Government she is a part-time radio host on WPFW 89.3 FM on the “Inside Out LGBTQ Show” on WPFW 89.3 FM. She also writes a column for Baltimore OUTloud under the column called “Trans Lives”. Karen received the Engendered Spirit Award from Capital Pride on June 7, 2018. She also was a TEDx Speaker with TEDx Asbury Park, NJ on May 19, 2018. In April 2017 she received the “2017 Monica Roberts Advocacy Award”. She was selected in January 2017 by LGBTQ Nation as one of the “Top 50 Successful Transgender Americans You Need to Know”. In May of 2015, she was honored in a special edition among 41 other women from around the world in The Platform Magazine, for up and inspiring females who have made a difference with their platform and inspired others with their positive values towards others. In April 2014 she received the “Willis Greene Community Service Award” and the “Unsung Hero Award-Team” by the Corporation for National & Community Service. In October 2013 she received “Soldier of the Year”, out of the country, by the State Guard Association of the United States out of 24 states and 23 thousand soldiers. In December 2012 she received “NCO Soldier of the Year” by the Maryland State Guard Association and The Maryland Defense Force. She was selected in August 2012 by The International Women’s Leadership Association, "A Woman of Outstanding Leadership in the Business Owner Division".

With the Maryland Defense Force under the Maryland National Guards she was a Staff Sergeant with Force Protection, the Chaplain’s Unit as a Chaplain’s Assistance, Honor Guard, and MWR. She has been doing volunteer work with the American Red Cross for the National Capital Region since 2009 on the Disaster Action Team. For several years, she has been volunteering with Community Emergency Response Team (CERTs) in Prince George's County, MD, and also with the Medical Reserve Corps. She sits on the board for the Retired Senior Volunteer Program (RSVP) in Prince George's County, MD. Karen also use to sit on the board for DC Metro PFLAG working with the Transgender Community. She is now the chapter president of the Transgender Veterans Support Group (TVSG) for Maryland. Before Karen’s transitioned, she previously volunteered with the Maryland National Capital Park and Planning Commission Park Police Prince George's County Division for 7 years, 5 of them as their President, and received several awards for her service, such as two Commander’s Awards and two Volunteer of the Year Awards. In December 2005 she received the Governor’s Crime Prevention Award for her outstanding work and leadership with Park Police Volunteer Association. She has her own side business called SafetyFirst DMV and is certified as an instructor through the National Safety Council (NSC). Karen believes whole heartedly in the importance of and Giving Back to her Community.