Thompson Island Outward Bound At Home Evening Expedition Gala

Our work has never been more critical than right now, in this school year, which is why we set an ambitious goal to reach 1,000 students through virtual learning, while we pave the way for a return to in person learning on the Island.

The Evening Expedition Gala is our largest fundraiser, and in a year when our organization will rely almost solely on philanthropy we are setting our goal high! We look forward to "seeing" you on October 7th @ 7:00 p.m. for our first ever At Home Evening Expedition Gala!

Quick Links

Program • North Star Award • Live Event Instructions & Tech SupportSilent AuctionEvent SponsorsAt Home Challenge ActivitySignature Cocktail


Welcome | Arthur N. Pearson, President and CEO, Thompson Island Outward Bound Education Center

North Star Award | Honoree: Mayor Martin J. Walsh, Presented by Garcelle, Thompson Island Student

Special Guest Appearances | Michael Chavis, Boston Red Sox, Enes Kanter, Boston Celtics, Brad Marchand, Boston Bruins, Gabby Thomas, Pro Track Athlete

Meet Our Students | Hear from Sentidra, Boston Public School Teacher and Thompson Island Outward Bound Alumna, plus other outstanding students.

Virtual Paddle Raise | Benjamin Farrell, Master Auctioneer, Custom Benefit Auctions

Closing Remarks | Mark Keating, Chairman, Board of Trustees, Thompson Island Outward Bound Education Center

Honoree Mayor Martin J. Walsh

Mayor Martin J. Walsh

The North Star Award symbolizes a guiding light of strength, integrity and leadership. In the past, mariners used the North Star to guide their boats across vast oceans. Tonight we honor Mayor Martin J. Walsh for his steadfast focus on improving education for all Boston students.

Mayor Walsh understands the importance of investing in education to eliminate the opportunity and achievement gaps that place too many barriers in the path of our students in the Boston Public Schools (BPS). Since he took office in 2014, we have seen an increase of $154 million in the annual school system budget. Mayor Walsh has extended the BPS school day, providing students in the district with 120 more hours of learning each year. Additionally he has improved access to education for our youngest and oldest learners – adding more tuition free pre-school and community college options. He also expanded summer learning opportunities to more than 14,000 children.

Source: Facebook @martyforboston

That was all before the COVID-19 pandemic. Since March, Mayor Walsh has been focused on ensuring the Boston Public Schools are providing the best education possible in the safest environment. That has included getting 32,415 Chromebooks and 2,600 hotspots delivered to Boston students. Additionally, he has allocated $80 million in new funding in the 2021 budget for the Boston Public Schools to meet the challenges of the pandemic while continuing to work towards closing the achievement and opportunity gaps.

We are grateful for the Mayor’s leadership on education and his inspiration to both the non-profit and corporate sectors to invest in and expand services that ensure all Boston youth have access to excellent education throughout their lives. We are honored to present Mayor Martin J. Walsh with the North Star Award tonight.

Source: Facebook @martyforboston

Live Event Instructions & Tech Support

  1. Visit event.gives/thompsonisland on your phone, tablet, or computer (for the best experience, use your computer). Everything about this event will take place right on your screen. If you’re watching with a group, we recommend that each person log in on their own device so they can bid and donate separately.
  2. Click the play button next to "This Event is Live Now!" to start the virtual event.
  3. Please log in to ensure you are ready to bid and fully participate in the program! Remember your cell phone number is your log-in credentials. If you forget your password simply click on “Text me a pin” or “Email me a pin”.
  4. Sit back & enjoy the program!

Technical issues? We have someone on standby for any technical issues, just use the blue QUESTION button on the bottom of the live stream video and they will respond ASAP.

This button will connect you to our event support for any technical issues!

Silent Auction—Open Now!

This year's auction is filled with something for everyone! Highlights include favorite local dining, fun day trips, family excursions, sports memorabilia, and more.

$500 Gift Certificate to Davio's
1/2 Day Fishing Charter in Westport, MA

Thank You Event Underwriters!

The Durant Family

Thank You Island Preservationist Sponsor!

Thank You Salt Marsh Restorer Sponsors!

Thank You Environmental Activist Sponsors!

Crowe LLPEaton VanceEpsilonFisher Phillips • KPMGLiberty Mutual InsuranceMassachusetts Convention Center AuthorityMassMutualMorgan, Lewis & Bockius LLPNutterRadius BankRBC Capital Markets • Someone Else's Child Foundation

Nancy and David Corkery • Sarah and William Ducas • Susan and William Elcock • Cindy and Ryan Enright • James Fitzgerald and Linda Shannon • Suzanne and George C. Gebelein • Mark and Sarah Keating • David S. Kirk • Jenny and Jay Leopold • Gordon R. and Kathleen M. Penman • Donald and Marjorie Swift • Gale and Charles Willauer

Thank You Coastal Conservationist Sponsors!

CBRE, Inc. • Comcast Business • Robert and Stephanie Cozzone • CrossCountry Consulting • Day Pitney, LLP • Dempsey, Lucey & Associates • Duff & Phelps LLC • Fort Point Associates, Inc., A Tetra Tech Company • Freeman • J. Calnan & Associates • Sandy and Louise McGinnes • Kate and Sean Newth • Cheryl and Scott Pinarchick • Michelle and Aaron Rhodes • RSM US LLP • Solomon McCown & Cence

Thank You Ecological Ambassador Sponsors!

Samuel and Susan Barnard • Jeanette Callahan • Margaret A. Coleman • Eddie J. Jenkins, Jr. • Red Sox Foundation

At Home Knot Tying Challenge


For all participants to tie the knot described.

You Will Need:

  • 1 piece of rope, about 18” (if you don’t have rope, be creative! A shoelace or ribbon, headphone cord, or dog leash are all options)
  • Knot cards (like these printable ones)


  • Ask for a volunteer to lead this activity.
  • The Leader picks a knot card and studies it.
  • Without showing the knot card to the participants OR calling the knot by name, the Leader verbally describes to participants how to tie the knot.
  • If participants are in person, sit back-to-back or in different places so you do not see each other’s efforts.
  • If using Zoom video-conferencing, have each participant turn off their video while they are following instructions so progress cannot be seen.
  • Try to complete your knots within 5 minutes!
  • When your time is up, have each participant first show each their results. Then, show the original knot!


Participants can tie knots silently with no questions allowed OR allow two-way communication between the Leader and participants. Set the expectation at the beginning of round. It all depends how much you want to challenge the Leader and participants!

A variety of debrief questions:

  • What directions did you find easy to follow?
  • Was there anything hard to understand, or that you couldn’t do?
  • Were there any surprises?
  • What did you learn about yourself?
  • What did you learn about your fellow participants?

Signature Cocktail

The Moscow Mule

  • 1/2 oz Craft Moscow Mule syrup
  • 1 1/2 oz of your favorite vodka
  • 3 oz seltzer
  • Stir over ice and garnish with fresh lime!

Option if you don't have the Craft Moscow Mule Syrup

  • Juice of ½ a fresh lime
  • 1 ½ oz of your favorite vodka
  • 4 oz any Ginger Beer
  • Stir over ice and garnish with fresh lime!

Or challenge your taste buds with one of these variations:

  • Moscow Mocktail — Skip the vodka and add a splash more seltzer.
  • Mexican Mule — Swap the vodka for your favorite tequila.
  • Kentucky Mule — Substitute vodka with a spicy bourbon.
  • Apple Cider Mule — Get in the fall spirit with a splash of apple cider.