Let's start with Wolfe Park. This sprawling town park boasts rolling lawns, multiple playgrounds, tennis courts, soccer fields, hiking, a lake for swimming and paddle boating, plus a pool.  It is massive.  It’s got such a different vibe than other parks in Fairfield County — here, I get the sense I am ‘inland’.   With children a few years apart, I loved being able to accommodate them simultaneously — kicking a soccer ball around with my 6-year-old, while keeping an eye on my 3-year-old enjoying the toddler playground right next to us.   Most astounding of all .. it’s free to non-residents.  All you have to do is park in the non-sticker designated lot — in other words walk a 100 extra yards to have ALL THIS.  (However, if you enter on the Great Hollow Lake side of the park, you will have to pay a $10 entry fee — in summer only.  The newly renovated pool also charges admission, but no shock there.)

A wonderful spot we’ve come to love is the Webb Mountain Discovery Zone.  It’s one of the few places I know in Fairfield County where you can go on a proper hike with young children.  Webb Mountain is not the easiest place to find, even with the signs planted along the way, so do NOT try winging directions with your cell phone as you drive.  Upon arrival, find the trail head and choose whether you want to stick to the easy route (manageable with a jogging stroller), or the more challenging paths.  Before you set off, grab the awesome little scavenger hunt cards and a pencil to give your hike some focus.  Or, just let them run free.  Or equally good -- make it a weekly event by signing up for one of their affordable Mommy & Me or preschool classes.  No matter what you do, just remember to do a tick check before you head back to the car.  For a more detailed day trip to Webb Mountain Discovery Zone you can click here.

Not far away, is the original part of this spectacular land parcel, Webb Mountain Park.  Take your teens here, and you’ll all be rewarded with a grand overlook of the Housatounic River, and maybe even some conversation.  Maybe.

If your teen would rather be on a bike, try the Housatonic Railbed Trail instead.  It runs from Purdy Hill Road along Great Hollow Lake’s access road, to a stone dust trail winding up to the Newtown Line — all told, around 4 miles one way.  You’ll work up an appetite...

Soup Thyme cranks out delicious soups and sandwiches, but if you’ve got young children in tow, it’s imperative to get there and get situated ahead of the lunch crowd … or risk all sorts of stink eye.  Even closer to Wolfe Park and the Railbed Trail is Purdy Hill Bakery & Deli, which, let’s face it, is more bakery than deli (and thank goodness for that).  Even still, choose from a wide selection of high-quality cold cut sandwiches before attempting to choose one dessert from the sweets case.  Impossible. (Also of note, there are peanut and gluten-free options on the menu). Or you could always grab a hero (grinder) at Gaetano's, an Italian deli with locations in both Stratford and Monroe with to-die-for sandwiches. Try the Kovac's Special. You'll thank us. 

If you happen to start your day trip around noon … and on a Friday ... when you’re done playing, plan to swing by the great little Farmers' Market on the Town Green.  They’ve got a good thing going here — you can actually pull off dinner, with vendors selling grass-fed beef, fresh pasta and breads, desserts, and of course, fresh produce.  Some weeks they even have live music and children’s activities in and around the gazebo.  It’s modern life in a nostalgic setting — jump right in!

Originally published 8/4/14

Cover photo courtesy of the Monroe Farmer's Market