Mead Park - New Canaan
A fabulous place to play, and an even more fabulous place to eat lunch or dinner.  Spend an hour on the playground – which features a separate enclosed area for the smaller tykes – and then enjoy a delicious, nutritious meal at the fabulous Apple Cart snack pavilion.  Great food for both kids and adults.  Order the falafel platter – you’ll thank me later!

Mead Park, Park Street, New Canaan 06840

Twin Meadows Boundless Playground - Stamford 
Twin Meadows is a great playground for lots of reasons.  Its soft rubbery play top softens any tumble, and the play equipment is innovative and unique.  Kids can enjoy a great raft that rocks back and forth, lots of stepping-stones for climbing, as well as the traditional swings and slides.  Plus, many of the play features are designed to be suitable for kids with a variety of disabilities.   

800 Stillwater Road, Stamford 06902

Bayley Beach - Rowayton
My favorite part of this playground?  The view.  What’s better than finishing an hour at the playground by taking off your shoes and dipping your toes into the ocean?   If you’re not too cold after testing the ocean waters, swing by Brendan’s 101 for ice cream on your way home.  Delicious.  Bayley Beach has residential permit parking during the summer season, so be sure to check their webpage for up to date parking information.

Bayley Beach, Rowayton 

Accessible Playground - Ridgefield
No ocean view at this Ridgefield Park, but you won’t miss it!  Ridgefield’s Accessible  playground was designed to be welcoming to all children.  Specific design elements, such as the rubberized flooring and ramps, make nearly 70% of the play space accessible to children in wheelchairs or with leg braces.   And all kids and adults alike will enjoy the tranquil park setting and the innovative playground.

195 Danbury Road, Ridgefield, CT 06877

Bruce Park - Greenwich
Bruce Park playground is our family favorite in the Greenwich area.  The playground successfully separates the big kids from the little kids (so the big ones don’t trample the little ones).  Tetherball is always a fun activity, and the big boulders that line the playground are the best climbing attraction around.

Bruce Park Drive, Greenwich 06830 

Leonard Schine Preserve Natural Playground - Westport
If you’re looking for something a little different then the primary colors of traditional playgrounds, visit this Natural Playground in Westport.  All of the “equipment” is made from wood and other natural resources found on the 20-acre plot.  You’ll be amazed at how the kids delight in the novelty of a different style of play equipment.  Pack some Band-Aids – splinters come with the territory.

Glendinning Place (off of Rte. 57), Westport 06880

Wolfe Park - Monroe
This place sprawls and sprawls.  There are two playgrounds, at two different entrances ... a big, wooden one that even includes a sandbox for tots, or the more modern looking plastic one alongside the swimming hole -- even this one has equipment the tiny kids will enjoy (phew, mama).  Aside from the playgrounds, there are wide open grassy fields to play soccer, or you can watch baseball and the pool.  Perhaps the best part -- it has one of the least strict seasons requiring residency. Only in summer will you have to pay to enter.

285 Cutlers Farm Rd, Monroe 06468
 

Veres St. Park - Fairfield
There are no frills, and no views, but this place is clutch for the under 5 set. There are two playsets skewed to their size and capabilities -- in other words, no heart-stopping drop-offs for your 3-year-old to happen upon when you look away for 5 seconds.  The only drawback is they aren’t shaded, but there is a sandbox with trees to catch a break from the sun.  There are also swings, a picnic table, and enough street parking to satisfy the pre-nap crowd.  If you need it, there’s a port-a-potty, and you won't be the only mommy setting up a training potty in the back of your SUV. 

275 Veres St., Fairfield 

Devon's Place - Norwalk
Not only is this place accessible from the Stepping Stones parking lot (where you could spend the morning/lunch), but it has the holy grail of park setups -- a playground AND a splash pad.  Seriously, a summer day is good as spent when you trek here!

Mathews Park, 303 West Ave, Norwalk 06850
 

Cherry Lawn Park - Darien

This is really the motherlode of Fairfield County parks. Your eight year old will love it. Your two year old will love it. You will love it. (You'll especially love the clean public restroom!) Set alongside sprawling lawns, tennis courts, and a lovely pond and gazebo, Cherry Lawn Park  has everything. Really, everything. From a toddler playground filled with sand, little playhouses and a larger-scale playgym for the older kids complete with bouncy bridges and tire swings, this park is a family favorite. Plus, it's home to the Darien Nature Center. 
 

120 Brookside Road Darien 06820

Full Circle Playground - Trumbull

This playground not only offers kids plenty of opportunity for play, but also teaches kids about recycling. The playground, located on the grounds of the Trumbull Nature and Arts Center, was created from about 50,000 plastic laundry detergent containers rescued from landfills. The environmentall sustainable playground, spanning a 40 by 60 foot area, has everything from monkey bars to swings plus plenty of picnic tables perfect for an al fresco lunch. 

7115 Main Street Trumbull 06611

Dickinson Memorial Park - Newtown

Built in 2014, this relatively new playground known as FunSpace II offers plenty of cool features like built-in musical instruments, a zip line and climbing stones. There's also fun wooden play areas and a water space with sand. Plus, it's handicap accessible.

50 Elm Drive Newtown 06470

Vicki's Playground - Stratford

Built as part of the Where Angels Play Foundation playground project, Vicki's Playground is located at Pender's Field at Longbrook Park in Stratford. The bright Flamingo-pink playground is set alongside a pond filled known to harbor large turtles and fish. A separate playground offers a space for toddlers to play with a couple of swings. And in winter, the town of Stratford sponsors a free outdoor ice skating rink. During the summer months, kids can splash all day in the park's splash pad. 

Glendale Road Stratford 06614

Original Post on 4/14/12 by Katie McKnight

Photo taken at Leonard Schine Preserve Natural Playground courtesy of Ally Noel