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The Dempsey Challenge: Team Cuppa!!

Back in January of this year, I resolved to make more happen with my business this year. I was tired of beginning each year with goals that centered on my personal success and was ready to be a part of something bigger and to make my business part of something more meaningful. Already donating a percentage of each booking to CancerCare, I wanted something more active, more engaged…something that would require more than money, but also time and interest and I hoped to find something that could spread the word further than my limited sphere of influence.

And thus Team Cuppa was born!

I’d heard of The Patrick Dempsey Center for Cancer Hope & Healing (you can’t really spend any time in a cancer center in Maine for any reason and not have heard of it!), but I didn’t fully grasp what it was. So I scheduled a meeting with a member of the amazing staff and spent an afternoon touring the facility and talking with the incredible people who work there. I was blown away. On every level.

Not only is it a warm, welcoming, beautiful space that emanates gentle healing energy from every nook and cranny, but it is embracing in every conceivable way. The mission is to support anyone affected by cancer in any way. So patients and survivors, certainly, but also family members, friends, co-workers…anyone affected by cancer in any way. There is reiki and massage. Nutrition classes and yoga. Support groups and counselors. Resource counseling and an extensive lending library. Their program offerings are ever expanding as the Center finds new and innovative ways to extend their integrative services in order to strengthen and heal the cancer community.

And they do it all free of charge.

That is huge. Crazy huge. Out-of-this-world-huge.

I know I shared a bit of my own story with cancer, but I cannot overstate how devastating and overwhelming it is to not only be faced with a life-threatening disease, but how to pay for getting what might save your life. Not just drugs, but care. Real care. Help navigating the complicated decisions and emotions. Identifying what support services are available. Coping with the side effects of a disease that affects more than just the person diagnosed, but their entire community of friends, family, and support…all those people who are caregivers in some way, whether big or small, and side effects that range from nausea to diminished income.

When I announced that Cuppa was going to have a team take part in the Dempsey Center’s largest fundraiser of the year, The Dempsey Challenge, I had no idea if anyone would take part. I had this fear that I would be knocking on doors with a can, begging for donations as the sole member of Team Cuppa. How could I have so underestimated all of you? Not only was I not alone in this endeavor, but the level of support and enthusiasm was just incredible!

Ali & Cesar came down from Canada for the event. Diana & Luigi came up from Manhattan. Kerri & Phil got their families involved. Josee brought her entire family to be the cheering section for everyone! And donations poured in from all of you who couldn’t make it. Former clients. Parents of clients whose weddings I shot years ago. People I’ve never met. We even had a 2014 couple go through the team roster and donate to each person so that every single member of our team would make the participation minimum and be able to take part on race day, donating several hundred dollars in total even though they couldn’t personally make the event.

And with all of that effort and pouring forth of love and support, our team raised more than $5000 total.


That total comes from people choosing to give rather than go out for dinner. To give rather than buying those new shoes or that new purse. To give rather than putting it into their personal travel fund. Or retirement fund. Or wedding fund. There are a million things that we could choose to spend our hard earned dollars on every day, but you guys put $5000 of yours toward the welfare and benefit of others.

You amaze and move me more than you could ever know and I am deeply grateful for every single one of you. Thank you. Thank you.


Justin and I hosted a little bonfire & s’mores Friday evening to kick off the weekend’s events…and I had my first-ever Reese’s peanut butter cup s’mores. Game changer, that one.

Who knew that glow sticks would e such amazing entertainment?!?!

Even Talitha & Josh stopped by, having just returned from their honeymoon in Aruba!!

Saturday morning the run came bright & early, but everyone showed up smiling and ready to rock! I’m sure that it had nothing with the possibility of spotting McDreamy!

Go Team Cuppa!!

Diana even made signs!!

Kerri’s whole family joined the Team!!
Ali & Cesar came down from Ottawa for the event!!
The little girls kept us all laughing and were more than happy to make sure that we didn’t have donuts leftover to go to waste!
So. We set up our tent Friday evening and when we left it, it was alone in the field designated the “team tent” area. When we arrived Saturday morning, it turned out that the “Boot Camp Challenge” (you know, the world’s most gigantic bounce house EVER) had set up directly beside us. Hilarious.

Messages of love and support written on fabric flags were strung across the bridge before the finish.

Ali & Cesar re-enacting the bridge shot from their Ottawa engagement session…so funny!!

With that, Team Cuppa’s inaugural Dempsey Challenge is behind us!! I’m already brainstorming ways to make next year even better…as soon as 2014 team registrations open, Team Cuppa 2014 will be ready!!

THANK YOU!!!!!!!


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KerriOctober 16, 2013 - 8:59 am

It was a great day. Looking forward to next year!

AliOctober 16, 2013 - 9:23 am

Such a great weekend! Thanks for pulling it all together, Cindy!

LiciaOctober 16, 2013 - 9:25 am

We had a wonderful time ! Looking forward to next year. You are an amazing, very inspiring person. You, and Justin, make it easy for us to want to take part. So, thank you !!!

ShannonOctober 16, 2013 - 12:19 pm

This is so awesome!! Looks like you guys had a great time. These pictures are so inspiring! Hopefully next year I will get to be there in person! Go Team Cuppa!

Diana & LuigiOctober 16, 2013 - 5:37 pm

Yay!! We had such a fantastic time, Cindy! So happy we could be a part of it. Looking forward to next year!

BeccaOctober 16, 2013 - 9:29 pm

This is amazing, Cindy. You are such an inspiration!

JustinOctober 17, 2013 - 11:04 pm

Phenomenal turnout for Team Cuppa!! Great to see some friendly faces from weddings past and meet some amazing new people to welcome into our “circle of love.” It’s so humbling to receive such an outstanding turnout (both directly and indirectly) from friends and family. As always, Cindy is the glue that brings greatness together and makes me proud of her everyday. I can’t wait for next year!

Carrie & Katy: Bar Harbor Inn Wedding!!

As you might imagine, I’ve been to a few weddings. One or two, you know?  And I’m always really struck by those couples who have so clearly created a real deep down community for themselves…often there is family involved, but there are also friends. Not just friends, but Friends. With a capital “F.” The kind who offer unwavering support. The kind who  show up. Every single time. Even when it means moving your stuff…again. Even when it’s not convenient.  Even when you are getting married halfway across the country from where they live.

Every. single. time.

Carrie and Katy spent their wedding day surrounded by just that kind of community. To look at the crowd of people around them and see face after face turned toward them filled with love and utter joy…and as is only proper given the percentage of them who happen to also be brilliant university professors, some seriously witty banter!

There was laughter. There was dancing. There was LOVE. And, to cap it all off, there was brunch.

Sounds like a pretty awesome party to me. So without further ado…Carrie & Katy’s Bar Harbor Inn wedding!!

Despite the clouds rolling in and threatening, the rain held off…I love a little misty ceremony!

Katy’s nephew, the ring bearer, couldn’t contain his excitement and just wanted to run to her! The rings, however, had been attached to the pillow (had being the operative word!)…a few minutes of searching in the grass made for a quick ring recovery and an awesome wedding day story!

Plenty of tears and laughs…and the Margaret Todd as the backdrop!

Carrie tied all of the “monkey fist” knots that decorated their wedding herself!

Seriously. Hilarious. I will never ever hear “Total Eclipse of the Heart” again without thinking of this dance number!

The Mount Holyoke crew…

Such a great day!!! Thank you so much, Carrie & Katy!! You guys are awesome!

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Carrie & Katy: Mount Desert Island Windjammer Sail!!

When you have family and friends traveling from all over the country to magical Mount Desert Island for your wedding, what better way to introduce them all to the stunning Maine coast than with a sail aboard a windjammer? Carrie and Katy decided to forego the traditional rehearsal dinner in favor of joining their guests for exactly such an adventure on the Margaret Todd! It was flapping sails and the open sea for these two!

The Margaret Todd boasts her very own mascot, a sweet Newfie named Maggie!!

Carrie & Katy have an incredible circle of friends and family…there was SO. Much. Laughter. on this trip out to sea!!!

Katy & Carrie!!! Lookin’ good with the wind through their hair!

What a phenomenal experience!! Don’t go far…Carrie & Katy’s Bar Harbor wedding is coming up next!!

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