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.
Our children have been gifted with incredible teachers at every level of education. From infant daycare, to Montessori preschool, to public elementary school, we have found wise, talented teachers happy to partner with us in educating our kids. Each has shaped their lives in ways that are already visible, but whose full impact we might not know for years. Grateful, grateful, grateful.
Naturally, I wanted to find a way to keep these teachers close over the years, and that’s how we found our way to the graduation book tradition. You’re probably already familiar with it – parents choose a picture book and ask their children’s teachers to write a note in it each year, kind of like a yearbook. As a words gal, I love the idea of capturing memories and hopes for the future from these dear ones. June’s book now has several years of notes penned inside, and Shep’s has been broken in by his beloved preschool director. They’re both already on the short list of items I’d save in a fire.
While this tradition isn’t a new idea, it’s become a beloved one in our family, and so I thought I’d share a bit about it today!
How to organize a teacher picture book signing tradition
Though this tradition requires a bit of sustained effort over many years (your child’s entire K-12 education!), it’s really an easy lift: once you’ve chosen a book (see below!), you simply have to produce it at the right time each year for the teacher to sign – and, perhaps more challenging, keep it safe all the months in between. (We keep ours in our children’s memory boxes.)
Here’s the email I send to our kids’ teachers in late May:
Hi [teacher name]!
I hope you’re enjoying these last few days with your students! I will be sending in a picture book soon that I’m hoping you (and [assistant’s name], if she’d like!) would be willing to sign for our girl! I’m sure you’re very familiar with the tradition, but the idea is that you’d both choose any page and write her an encouraging note (no need to return it the same day – anytime before the end of the year!). We’ll then pass the book on to her teachers next year and beyond. (We do plan to let her read it along the way instead of waiting until graduation!)
She has enjoyed being with you both so, so much this year, and I know it will mean the world! Thank you in advance!!
Emily
Once receiving confirmation, I tuck the book in her backpack inside a manilla envelope. We keep it close until the end of the school year, then let the kids read the notes at our end-of-school-year/beginning-of-summer celebration. (I know some parents keep the tradition a secret until senior year, but I think it’s meaningful to be buoyed by these special teacher’s words along the way!)
14 Great Graduation Book Ideas
When looking for a graduation picture book, the key is to combine a meaningful message with illustrations that leave enough white space for writing notes. This is surprisingly tricky to find! Here are the two books we’ve used for our older kids, and a few others that are worth a look:
— The World Needs Who You Were Made to Be by Joanna Gaines | This is June’s book! I wouldn’t say it’s the absolute best story, but it’s sweet, the illustrations are lovely, and it has plenty of room for writing.
— What Do You Do With an Idea? by Kobi Yamada | Shep’s book! The black-and-white illustrations work wonderfully for adding colorfully-penned notes, and the message is timeless.
— Miss Rumphius | In terms of messaging, this would be my hands-down choice – but alas, I didn’t think it had enough room for notes. Worth considering, though!
— Oh the Places You’ll Go by Dr. Seuss | A classic! The sales of this one must be bananas in May.
— A World Wonder by Laura Wifler | Though I haven’t chosen a book yet for Annie, this is on my short list! We love this story of a girl with big dreams on a journey to discover what makes life truly meaningful.
— Journey by Aaron Becker | This is a visually-stunning wordless picture book – perfect for adding your own words of wisdom over the years!
— The Wonderful Things You Will Be by Emily Martin | This seems to be a very popular option for graduation book gifts. I don’t care for her illustration style as much as some of these others, but this is a great pick with plenty of white space on the page.
— All the World by Liz Garton Scanlon | This simple, profound Caldecott Honor book follows a circle of family and friends over the course of a day. The breathy, windswept illustrations leave plenty of margin for notes!
— Because by Mo Williams | We have and love this picture book about the chain reaction one decision can make, which begins and ends (and begins?) with a life-changing musical performance. Check it out in person, though – the (beautiful!) illustrations take up a lot of the space on each page.
— The Day You Begin by Jacqueline Woodson | The vibrant illustrations in this one are a marvel, but I don’t know that they leave quite enough room on the page for notes! Either way, the message is lovely and this is a book my kids enjoyed reading.
— Wherever You Go by Pat Zietlow Miller | This one seems a bit calculated to be an alternative to the almost-trite Oh the Places You’ll Go, but I think it succeeds! The verse is easy, the illustrations are whimsical and packed with detail, and it has plenty of “off you go into the world!” verve.
— The Giving Tree by Shel Silverstein | Sob. This unforgettable story of love and empathy is a timeless pick. Shel’s spare, black-and-white illustrations leave plenty of room for colorful penned notes.
— Why Not?by Kobi Yamada | Honestly, this one seems designed to be used as a graduation book rather than as an actual picture book for preschoolers, so let’s give it its moment! :) The beautiful illustrations and encouraging text are an invitation to embrace big possibilities.
— The Three Questions by Jon J. Muth | “When is the best time to do things? Who is the most important one? What is the right thing to do?” These questions are asked and answered in this picture book based on a fable by Leo Tolstoy. Simple and direct text paired with whimsical watercolors make for a satisfying package.
I’d love to hear: does your family do the graduation book tradition? If so, what books do you use? I’d love to hear!
Hello, friends! I hope you all had wonderful Thanksgivings. We were in Virginia with John’s family and the week left me feeling full and happy. We decorated sugar cookies, we played cards and Do You Love Your Neighbor, we went on a hike, we went into DC and had tea, and our Thursday table was full of all the usual favorites plus buttered noodles, a Thomas family tradition.
Perhaps my favorite part, though was the walks. Every morning, any adult siblings who were available snuck away for a brisk walk, 30 minutes to an hour. Not only did it feel great to move my body throughout a week that is more often known for lounging and eating, but the power of walking and talking was on full display. We filled each other in on jobs and home projects, kids and parents, travel and health and plans for next year. I am grateful for the siblings I married into, and relished the opportunity to catch up with some of my favorite people in this way. I hope you were able to find moments of connection this week, too.
To wrap up this year’s gift guides, I thought I’d share a few of the items I’ve squirreled away for my family’s stockings. Linking is a bit difficult, since I prefer to pick up items throughout the year as I visit small shops and boutiques, but I’ve noted the same or similar items where possible. I hope it’s helpful! (And if you want to finish your shopping in one go, don’t forget about my friends’ ingenious one-stop stocking shop, Persnickety Gifts!)
Annie:
— A new water bottle and a handful of stickers from our summer travels to jumpstart decorating it — Color-changing flame packets for s’mores nights (I’ll split these up between the kids!) — A kitty pencil pouch for all her treasures — An adorable little deer stuffie — Fairy house supplies from our local garden store — A sheet of Bluey stickers — A Liberty fabric knotted headband — A few Schleich animals — Hair elastics — The most fun bandaids — Some sort of candy
Shep:
— A handful of Yoto cards stored up from our subscription — A roll of Scotch tape, since he’s forever borrowing mine — A mini paper airplane set — Cherry sour balls from Michigan favorite Cherry Republic — The most adorable little lantern. (All of the kids are going to go nuts for this and I probably should have bought three…) — Tattly dino tattoos — 50 silly scavenger hunts — A camo tank and camo jeep — A new paint-by-sticker book, his favorite — Glow in the dark stickers — A few new Hot Wheels (I think I’ll see if there are any on our neighborhood Buy Nothing group!)
By popular request, I’m transposing the conceit of my gift guide for kids to this one – gifts for the people you love – by sharing what I’m actually gifting to a few of the loveliest people in my life this Christmas. Plus, I’ve included a few notes on gifts that have landed well in the past, in the hopes that one might be the right for your husband, mom, dad, sister, in-law, or beloved teacher.
(And on that note, if you are any of those people, close out this post pronto. Please and thank you :))
In the past, I’ve gifted experiences (Jim Gaffigan, Nate Bargatze, a treetop adventure course), this chair that folds up tiny, LOTS of clothing (this, this, this, this, this, and this most recently), a tumbler, a Durham Bulls shirt, a NYT crossword puzzle book, a Soda Stream (still used daily four years later), a weather station, and a very suave briefcase. (The briefcase linked is not exactly the same, but as close as I could find from the same brand – I bought John’s in 2018. It’s been used daily and still looks handsome!)
In the last few years he’s also bought himself a ruck carrier and plate, a down coat with hood, a fleece jacket and hat (both seen above), and some Ugg boots – after lusting after my warm toes for years. And don’t forget this post on some of John’s clothing favorites – lots of good ideas in there! One to highlight: the Legends sweater shirt, which is still his favorite thing to wear. Looks like a flannel, is as incredibly soft and stretchy as the best sweatshirt.
Oh yes, and don’t forget books: though John doesn’t read a ton of them himself (he’s more of an articles guy), he loves to support his favorite authors and thinkers by adding their offerings to the collection on his nightstand :) A few new additions this year: Fighting Shadows, The Divine Conspiracy, The Anxious Generation, and How to Know a Person.
My Dad will get a continuation of the Atlantic subscription I started for him a few years ago, and whose articles we enjoy discussing together – though I’m intrigued by this grill prep and carry set that is being gifted by several members of Articles Club this year.
For his Dad, John chose a gift basket of food goodies from Asheville. It’s a little more than the limit (see below), but it’s in support of our beloved mountains, so we’ll just consider the overage a donation :)
On John’s side of the family, the siblings and parents draw names — everyone gifts to one other person with a $100 limit. I drew my mother-in-law and chose for her a weighted vest (I got the 6 lb version!), a stick-on bird feeder, and the cutest seed birdhouse from a local garden store (above!).
On my side of the family, the siblings and husbands have opted to splurge on a fancy dinner out, together, in lieu of gifts over the last few years – and this year, too. However, my younger sister Kim will be joining us for Christmas morning this year, and per my desire to leave no one out of the gifting, I’m planning to wrap up a few small things for her: a set of 2025 PowerSheets (perk of the job!), a caramel tasting set from Trader Joe’s, a watercolor workbook, and a Ghiradelli’s brownie mix paired with a little bottle of blood orange olive oil. (You swap the flavored olive oil for the canola oil called for in the recipe – so delicious!!)
My Mom is going to get this Blackwatch pullover from my own wish list – she likes most of what I like and as a diehard New Englander, loves an L.L. Bean gift :)
All of the kids’ teachers will be getting a gift card to a local business, matched to their interests, and a very grateful note.
A few other gifts we’ve given in the past for your consideration:
— Chappy Wraps | Light yet cozy with the prettiest patterns. This is the go-to blanket on our sofa and we’ve gifted one to my parents, too!
— Original Bogg Bag | We use ours at the pool, the beach, and the soccer field, but I think they’re particularly helpful for road trip packing.
— Snap tote | They fold up flat and snap open to fit a ton – I use mine at least weekly, and have had it for years!
— Boat & Tote bags | Incredibly sturdy and incredibly classic. I like mine open top, in navy, with sans serif embroidery. I find this to be a versatile gift at a great price point that’s easy to personalize – you could embroider her initials, nickname, or something funny or practical! Plus, they introduced the most beautiful medium blue this year!
— Geometry napkins | I split two packs of these between my Mom and I for Mother’s Day this year, and they were a hit with both of us! The suede-like material requires no ironing for a smooth fold and there are dozens and dozens of patterns to choose from.
— Something meaningful, framed | We recently gifted John’s parents a house portrait as a housewarming gift and framed it with Framebridge – a favorite I’ve used for many projects over the years. There are lots of house portrait options on Etsy, too!
— Solo stove | Yes, this gift was all the rage a few years ago, but it’s still worth a mention! Produces a near-smokeless fire in a compact, good-looking package. Pair with extendable sticks and the absolute best thing to sandwich a marshmallow between.
— Tea kettle | An elegant countertop tea kettle for the tea, coffee, or hot chocolate drinker in your life! We’ve gifted these twice and they’re always a hit. Lots of fun options for this one – pair it with some gourmet or meaningful tea or coffee, a pretty tea towel, and/or a mug that will make them smile!
— Something from White Flower Farm | This is my father-in-law’s favorite plant source, and we have ordered many things from them over the years! Bulbs, wreaths, flowering houseplants – or a gift card for them to choose something for their yard.
— A photo gift | Don’t sleep on the photo mug, friends! Are they a little cheesy? Yes. Do lots of grandparents legitimately want one? Absolutely yes, but they’re not, you know, something you’re going to buy for yourself. A personalized calendar with photos from the year is another sure bet!
— A live wreath | This was our go-to teacher gift for several years running – we bought simple wreaths from a local fundraiser and dressed them up with bows. I have also done the same for hostess gifts! L.L. Bean has beautiful options if you need to ship.
— A media subscription | Whether physical or digital, this is one of my favorite things to give. In recent years, I’ve given an Our State subscription to a friend, an Atlantic subscription to my Dad, and a So Many Thoughts subscription to my Mom.
— A digital picture frame | The siblings went in on this for John’s parents a few years ago, and it’s so easy to upload new photos by email!
Whew!! I sincerely hope you found an idea in there for the ones you love, or that something I listed sparked an even better idea. And happiest Thanksgiving, friends! I’ll be back with a final gift guide on Friday :)
