The Vermont Principals Association
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The Vermont Principals’ Association is inviting you to the 2024 Winter Symposium at the beautiful and cozy Woodstock Inn for colleagueship, rejuvenation, inspiration and meaningful professional learning.

  • Who: The target audience is school leaders, central office administrators, athletic directors, and aspiring school leaders
  • When: The evening of Sunday, February 4th & Monday, February 5th
  • Cost: $450. per participant. The cost includes 9 hours of professional learning, all related session materials, Sunday evening desserts, breakfast and lunch on Monday. The cost does not include any overnight accommodations.

Picture of Jennifer Berkshire

Keynote Jennifer Berkshire: is the host of the education podcast “Have You Heard” and the co-author of A Wolf at the Schoolhouse Door: the Dismantling of Public Education and the Future of School. Her writing on education and politics has been featured in the Nation, the New Republic, the New York Times and other publications. She teaches in the Boston College Prison Education Program and the Education Studies program at Yale. Her new book, The Education Wars: A Citizen’s Guide and Defense Manual, will be out in 2024.

Keynote Julio Delgado: is a Leadership Executive Manager for Apple Education for the Eastern half of the United States. He has served in K-12 public education for 34 years as a School Psychologist, Vice Principal, Principal, Coordinator and Director of Special Education and PPS, Assistant Superintendent for Curriculum and Instruction and Deputy Superintendent. Skilled in Curriculum Planning and Design, Educational Technology, Leadership Coaching, Equity, Diversity and Inclusivity Leadership, Strategy Creation, Instructional Coaching, PLCs, Classroom Management, Special Education, and Public Speaking. Graduated from St. John’s University and Queens College. He has spearheaded initiatives that foster creative instructional design, team building, teacher leadership, social emotional wellness, diversity, and equity in school planning.

February 4th, Sunday Evening: Participants will gather in the Rockefeller room for networking and a BOOM session from 5:00pm to 6:15pm. The BOOM session will feature 6 different presentations about an outstanding and exciting practice direct from a school leadership colleague. Each presenter will have 8 minutes to share about an innovative and effective practice that is in place in their school setting. Prior to the BOOM sessions dinner will be on your own. You can enjoy a nice meal at the Inn or once of the many restaurants in the picturesque town of Woodstock. Later that evening we invite you to join us for a social time with colleagues, desserts and a cash bar from 7:45-9:30pm. 

February 5th, Monday: Participants will have breakfast available 7:00 – 8:00 am. Our morning keynote will be author and podcast host, Jennifer Berkshire. You will then have two opportunities to attend breakout sessions open to individual choices. Each workshop will run in the morning, and in the afternoon, so if your top choice is full in the morning, you can select a different choice and then try again in the afternoon. We will end our day with a closing keynote by Apple Executive, Julio Delgado. Lunch will be provided mid-day and we plan to have people on the road around 3:30 pm on Monday afternoon.

Workshop Session Options

Cultivating a Thriving Educational Ecosystem: Strategies for Supporting Staff, Fostering Culture, and Empowering Teacher Voice & Leadership” with Principals Holly Roulle and Rebecca Fillion
Join us for an enriching workshop designed to empower educational leaders, administrators, and educators to create a supportive and innovative school environment. We will explore a wide range of topics, from optimizing systems and communication to enhancing culture and promoting teacher voice and leadership. This workshop is a valuable opportunity for educators, administrators, and school leaders to come together, share best practices, and gain insights to enhance the educational experience for both staff and students. Let’s work together to build a thriving educational ecosystem that promotes growth, innovation, and a sense of belonging within our educational community.

The Opportunity of Technology in the Classroom, Apple Education

Is your technology doing enough for your students and teachers? What does “enough” look like? Join us to discuss how technology can improve teaching and learning, along with best practices for supporting your vision for technology at scale.

Unlocking Your Potential: Creating Possibility Boards with Dr Jacqueline Sanderlin

Are you ready to transform your dreams into tangible realities? Join Dr. J for an engaging and transformative workshop where you’ll learn how to craft your very own Possibility Board, a powerful tool for manifesting your goals and aspirations. By the end of this workshop, you’ll leave with a beautifully crafted Possibility Board and the knowledge and motivation to turn your dreams into reality. Don’t miss this opportunity to ignite your potential and take the first step towards a brighter future. Join Dr. J and embark on a journey of self-discovery and empowerment. Note: Please bring any personal photos, images, or materials that inspire you, as well as your enthusiasm for personal growth and transformation.

Outline Schedule

Sunday, Feb, 4th  
4:00pmRegister and Check-in for participants staying overnight    Woodstock Inn

5:00 – 6:15Boom SessionRockefeller Room
6:15 – 7:45Dinner on your own Woodstock Inn Dining Options, Area Dining Options
7:45 – 9:30Desserts & cashbar Rockefeller Room
Monday, Feb, 5th  
7:00 – 8:00amRegistration & BreakfastRockefeller Room
8:00 – 9:15Welcome and Opening Keynote with Jennifer BerkshireRockefeller Room
9:15 – 9:30Connect with Vendors and Transition to WorkshopsDownstairs Hallway
9:30 – 11:30Workshops Session 1Downstairs Breakout Rooms
11:30 – 12:15Lunch & Connect with Vendors
12:15 – 2:15Workshops Session 2Downstairs Breakout Rooms
2:15 – 2:30Connect with Vendors and Transition to Closing Keynote
2:30 – 3:30Closing Keynote with Julio DelgadoRockefeller Room
3:30Safe Travels Home


What about the cost? The VPA has worked with Woodstock Inn to help keep costs down for this event. By holding the event on a Sunday evening and Monday, the Woodstock Inn was able to offer a much reduced rate for use of the venue and the room reservations. 

Do I need to attend Sunday Night? No, but you should! It is going to be a great networking opportunity, fun, and will have great take-away ideas and strategies for school leadership.

Do I need to stay overnight at the Woodstock Inn on the 4th? No, but there will be rooms on hold for participants attending this event at about a 40% reduced rate.

Will any of the sessions be hybrid in case I can’t attend in person? No, these sessions will be available in-person only on this occasion.

Cancellation Policy: For all Vermont Principals’ Association professional learning events, the VPA must be notified of any cancellations no later than 10 days prior to the event. Cancellation notifications received after the 10 day deadline will be subject to a fee of 50% of the total cost of registration. The reason for this 50% policy is it allows us to at least recoup the venue and food costs counts for the event which are locked in with the venue about ten days ahead of an event.