Planning a 20th high school reunion

If you’re a Connected Family reader, you already know that our twentieth high school reunion was an incredibly memorable and completely delightful weekend. I waxed philosophical about it at length last month, so I won’t reprise it here — but I did want to share some of the logistical details in case you’re thinking of planning something similar! Much of what we did could be applicable to a girls’ trip, a bachelorette, or a special family adventure. I’d love to share a little bit about how it all came together and a few of the details that made it special. Let’s go!

Planning Timeline:

Noticing that our twentieth high school reunion was approaching and that our class wasn’t planning an official event (at least at the time — they have since gone on to hold a low-key get-together!), John and I sent an email to our group of 11 close friends to see whether they’d be interesting in gathering the following summer last September. We’re spread out around the country, so even though we love each other dearly we weren’t sure how feasible getting together would be. Happily, the enthusiasm was resounding, so my next step (in December) was to send out two possible weekends for a vote.

Once the responses rolled in, we chose a date. We were originally interested in staying at a communal property, as I’m of the mind that some of the sweetest moments in a group happen in the in-between times, but the place we had our eye on wasn’t available. Most folks opted to stay with parents who still lived in the area.

From there, I got busy drafting an itinerary that was full of nostalgia but updated for our thirty-something lives, many of which now include kids. Happy to take the lead but not wanting to move forward without any other input, I sent out my ideas to two members of the group who kindly gave me feedback. With their blessing, I booked what needed to be booked. 

I sent out one more quick survey in March to nail down final details, confirming things like kids’ ages, arrival and departure plans, accommodation info, and what days they planned to participate in activities. Google Forms made this easy.

The week before we convened, I sent out a printed itinerary detailing the weekend’s fun. I also created a new text thread with all the attendees (original friends + spouses). This was super helpful for communicating details on-the-go throughout the weekend!

The Itinerary:

We were lucky enough to grow up in beautiful Southeastern Connecticut, and our schedule aimed to take advantage of all that we loved as teenagers — with a few concessions to our reality as thirty-something parents. Here’s how we spent our time:

Wednesday:

The Thomas family flew in late — we rented a car and got to my parents’ house after midnight.

Thursday:

With arrivals throughout the day, we had a leisurely breakfast at home and then drove out to my family’s farm to see several of my aunts, uncles, and cousins over lunch. The kids got to climb around in the hay barn and pet horses’ noses, always a hit.

After showering back at my parents’, we all headed to Tox Brewing in New London. Tox is owned by two of our classmates, Dayne and Mike, and though we didn’t see them when we were there it was fun to support their brand-new, larger location. We took over two long tables, ordered beer and wood-fired pizza, and chatted for 2+ hours. I brought original and preschool sticker books to help keep the kids happy. They also played several rounds of Go Fish and hit up the arcade games thanks to the benevolence of one of our childless friends (thanks, Uncle Jeremy!!). 

Friday:

Our favorite beach growing up was in Rhode Island (New England states are so much smaller than down South!), so we once again crossed the border and drove the 30 minutes to Watch Hill. While we preferred the more remote Napatree Beach in high school, we opted for the more-accessible public entrance near the Ocean House this time to lug our chairs, canopies, and sand toys. We stopped for deli sandwiches at McQuade’s on the way (another very nostalgic move) and enjoyed chatting, swimming, and eating for a few hours on a windy but warm and sunny day. 

After regrouping and showering at home, we drove over to Abbott’s for a seaside dinner. (The combo of beach day + quick shower + sunset seaside dinner are some of my very favorite days growing up — and still!) Longtime readers might recognize Abbott’s as the site of our rehearsal dinner, and it was fun to return there with so many of the friends who were with us on that happy day.

After getting the kids ready for bed and leaving them in the care of their grandparents, the grown-ups headed back out to the back deck of Jackie’s parents’ house. Our original plan was to gather around a fire pit and toast s’mores, but we never ended up striking a match — once we got to talking, we didn’t stop for almost four hours. (Don’t worry, we had plenty of snacks besides marshmallows.) This simple, uninterrupted time for deep conversation was one of my very favorite parts of the weekend – more here.

Saturday:

Another beautiful day and we started it with a short, flat hike at Bluff Point – perfect for little kids (we had 11 kids in our crew who ranged from age two to age nine), and nostalgic for those of us who ran cross-country (races were sometimes held there!).

From there, we headed to Mike’s parents’ house for a pool party in their backyard. My parents and his graciously provided lunch — pizza, fruit salad, cookies, and drinks — and we spent several hours splashing, eating, and chatting.

Later that evening the grown-ups met back up for our last major event, a fancier dinner out at Trattoria Amalfi. John and I got there a bit early to get the table set — see below — and it was once again the loveliest few hours of conversation and laughter. My cheeks hurt by the end.

Sunday:

We finished things off with breakfast at Sift in downtown Mystic, a very-welcome addition to town since our high school days. Our family had to scoot to the airport all too soon, but it was a happy chance for one more round of hugs and promises to not wait another twenty years to gather again.

A few ways we made this weekend special:

Of course, gathering with these dear friends was enough of a treat on its own — but you know me :) I couldn’t help adding a few extra details here and there, and I think they were both appreciated and really communicated that this weekend was an extraordinary experience — something to be savored.

First, I set up a communal playlist on Spotify. I seeded it with favorite songs from our high school years and encouraged everyone else to add to it, as well. We listened to it in the days leading up to the weekend and while driving along familiar roads, and it really set the mood.

I also designed, printed, and mailed a paper itinerary, and I think that helped communicate something special was in store. Canva made this super easy!

Finally, we added a few special touches to Saturday’s dinner. I chose a photo featuring each person, either from high school or the years since. I printed them all in black and white, attached them to thick white paper, and then watercolored each name on the bottom. On the back, I wrote a short note letting them know what they meant to me and thanking them for being here. These served as place cards at the dinner table.

At each place setting we also put a small box of chocolates from ATY Bonbons, a local treasure — just a little surprise to sweeten the journey home.

And there you have it! The nuts and bolts of a very special weekend. It exceeded my already-high expectations; I’d relive it a thousand times over if I could. We agreed to gather again in another five years, and it can’t come soon enough. 

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