For an ongoing collaboration between GOOD Morning Wilton and Trackside Teen Center, Trackside’s Executive Director Lori Fields, LCSW will contribute periodic columns to GMW about community wellness and engagement, mental health, Wilton teens and programming at Trackside. She’ll offer simple stories and inspired ideas to help us stay ‘on track’ to living a life that feels deeply satisfying and uniquely ours. Fields has a background in researching human behavior and potential.
Wilton Families,
Happy end of the school year. Happy graduation. Happy summer.
Happy — or maybe not-so-happy — adjusting!
School’s out and adjusting — to the school year ending and the anticipation of the next, to a change in schedule — brings with it a variety of emotions for everybody. Even when we welcome change, it can still take us a little time to find our footing.
The house will be messier, the kids will sleep later (or worse…wake earlier), they’ll use a new glass every time they get a drink (drives me crazy!), and they’ll say they’re bored over and over again. I always respond with “Awesome, being bored does incredible things for your creativity and imagination!” (cue the eye roll). Their screen time will likely increase.
As the summer season begins, it may also hit you like a ton of bricks that you’re exhausted. Whatever you’re experiencing, patience, kindness and flexibility go a long way, towards yourself and those around you, when adjusting to change — something I have to remind myself of regularly.
It’s also helpful to note:
Kids having nothing to do isn’t such a terrible thing.
And things like the house being messier, the kids being less scheduled, more snacking and less healthy meal eating, more free-ranging, etc. turn out to be not that big of a deal, especially in hindsight.
In fact, a change from the ‘same ole, same ole’ can feel like a relief and often leads to something surprisingly great.
Before your plunge into summer, take a moment to reflect on all the wonderful things that have happened this past year, give yourself a window of time where the rules are loose, and then:
- Be intentional about considering if there’s a ‘summer way’ of operating that works best for you. Maybe you’re craving regular evening walks, a solo trip to visit a friend, or a little more help on the homefront. Whatever it looks like for you, managing ‘all the things’ is easier once you’re grounded with yourself.
- Decide which few things matter most to you this summer. I emphasize “few things” because selecting just a few things that you really want to do, things that you’d be bummed about if the summer ended and you never did, helps reduce overwhelm and increases your chances of taking action.
You’re more likely to do two or three meaningful things than you are to check all the boxes of all the things you think you need to do to provide a great summer for your kids.
I happened upon a wonderful post on the Working Moms of Wilton Facebook page. A mom with younger kids was asking for advice from moms with older kids about what meant the most to their kids during the summer.
The responses were delightful, the common thread being that many of our most memorable and meaningful moments with our kids happen in the simple moments when we’re fully present and having fun with them.
Where you go, and how much time and money you spend, matter LESS than the quality of experience.
So take a deep breath, no need to panic or let overwhelm get the best of you as you think about your summer plans. There’s a whole lot of ‘special’ that can happen without having to work so hard or plan for it.
Our kids just want to have good times with us, even if they roll their eyes and give us a hard time about doing whatever it is we want to do with them.
We, at Trackside, wanted to help you have an easier time doing some fun things with your kids this summer so we put together a robust list of interesting, easy and fun things to do in the local area.
Do not look at this list and jump into beast mode, thinking you should do as many as possible. Do what resonates.
We wish you a fun summer filled with some really great memories.

MARIE DEMASI
Executive & Program Assistant at Trackside, AFSP Board Member, mother of three, social media wiz
Marie is heavily involved in the community, usually found front row for anything theater related, and an eating local “enthusiast.” Her favorite things about summer are road trip adventures and bonus time with her kids.
Marie’s Summer Faves
- Lots of ice cream! We love Heinbecks (S’moreo Sundae) and Ferris Acres (parent trap) but always try to find new shops
- Enjoy the North Fork: We roller skate and highly recommend Aldo’s for coffee, biscotti and a scone
- Spend a day in Mystic: Grab bubble tea at Alice in the Village; then head downtown to Sift Bake Shop for a macaroon, iced Arnold Palmer and Ebbioche (think croissant meets monkey bread)
- Hike at the Hidden Valley Preserve in Washington Depot, then pretend to be a Gilmore Girl in Washington Depot, Kent, and New Milford. Check out the Po Cafe and tell Maggie that Marie sent you.
- Play Mini Golf: one summer we hit up all of these CT mini golf courses
- Hit up a local farmers markets: My favorites are Wilton for Bubble & Brew‘s bubble tea, Westport for Ivy’s Granola, and New Canaan for fresh ravioli, Raus Coffee and more.
- This year we will finally get to Hershey Park!
- Walk the High Line in NYC and see a show. We just saw & Juliet and loved it. This summer we hope to see it again.
- See a live sporting event: My youngest daughter is going to see Manchester United.
- Attend a concert: We missed out on some good ones and I am having some serious Dave Matthews band FOMO.

LORI FIELDS
LCSW Executive Director of Trackside, GMW contributor, mom of three school-aged kids
Lori loves spending her summers shifting into low gear, upping her workouts, cooking as little as possible, finding fun DIY projects (especially with repurposed furniture) & spending lots of outdoor time with the kids.
Lori’s Summer Faves
- Hike the Waterfall Path at Saugatuck Falls
- Road Trip to Newport: Check out the Car Museum, Cliff Walk, Mansion Tour and the International Tennis Hall of Fame
- Backyard outdoor movie: Even better with friends.
- Pier 25 NYC, Tribeca: Skateboarding, mini-golf, beach volleyball, amazing playground with water for the kids.
- Enjoy a drink aboard Grand Banks, the oyster bar aboard the historic wooden schooner, Sherman Zwicker.
- Concerts in Ballard Park, Ridgefield: Pack the picnic blanket, lawn chairs, a bottle of wine and pick up pizza for the kids. Enjoy live music while the kids play at the playground. Every Tuesday and Thursday evening through Aug. 31.
- Need a few nights away, without the kids? Of course you do. This place is lovely.
- Rainy day… hit up the ‘IT Course‘ at Jordan’s Furniture in New Haven, then head to the cafeteria at IKEA for lunch. Will keep kids busy for hours.
- Mongers Market Flea Market, Sundays 10 a.m.-4 p.m.
- Beyond King Tut, the Immersive Experience, Hartford, Aug. 11-Oct. 15
- 4D Theater at the Maritime Aquarium: “BBC Earth’s Octopus“

FARAH MASANI
Founder of Wilton Pride, Trackside Board Member, active volunteer for the PTA, Boy Scout Troop 125 and Wilton Youth Council
Farah is a farmer, visionary and social justice advocate. She loves spending her summers sourcing real food, traveling, volunteering and supporting local, family-owned businesses.
Farah’s Summer Faves
- Cruise to nowhere: Ride the Greenwich Ferry for only $20. Visit Great Captain Island and Island Beach.
- Take a Thimble Island Boat ride
- Go on the Norwalk Sheffield Island Lighthouse and Harbor Tour
- The best summer bike ride is in Rhode Island; along the way you have to eat oysters at the Bristol Oyster Bar
- Make sure to visit Sport Hill Farm in Easton. Then visit Geiser’s, the town’s cutest cafe and market.
- Copps Island Oysters: Ask Norm to take you for a boat ride and learn about oyster farming
- Planning a summer BBQ? Custom Meats in Fairfield has the best meat in Connecticut
- Enjoy some fun family camping or head out a little further for the best glamping
- Take a drive to the dam at Croton Gorge Park in Westchester
- Take a hike: Climb the fire tower at Mt. Beacon or hike ‘The Gunks’ (short for Shawangunks) at Mohonk Preserve or other spots
- Farah and Shawn’s Date Night Favs: Chaplin in Shelton, Casa Me in Westport, and Tap Root in Norwalk
- Favorite Wilton trails: the Wilton Town Forest, Bradley Park and Weir Farm

JOHN PRIEST
Head of Programming at Trackside, Social Studies teacher at Middlebrook, dad of two
John loves spending his summer outdoors, listening to live music, family road-tripping, backyard BBQ’s, attending local events and planning for all fun things Trackside for the year ahead.
John’s Summer Faves
- John loves everything, especially local hikes, live music, scavenger hunts, local food and drink (Nod Hill Brewery, Milestone, Valencia), historical tours, and Jessie’s Girl (at Ridgefield Playhouse on July 22).
- There are a few seats left on Trackside’s summer trip to Colonial Williamsburg if your teen is looking for an awesome, immersive experience with John as their personal tour guide extraordinaire.