Connecticut Charmer: Ridgefield

Connecticut Charmer: Ridgefield

I have been wanting to visit the town of Ridgefield, CT for a while now. Not for any particular reason other than I keep hearing how perfectly bucolic the setting is, and what a charming downtown it has. Having grown up in CT myself not too far away, it amazes me how much of my home state I still have not seen. So when a friend recently came back from the day there with her family and said to me that I had to check it out, I slotted it in my itinerary for my girls’ next school day off the following week. She said that she and her family had gone to Ridgefield after a morning of apple picking, and so I planned the same: apple picking at Wilkens farm (see recent post here), followed by lunch and shopping in Ridgefield.


Located in Fairfield County about 60 miles from New York City, Ridgefield is about as Connecticut quaint and New England as they come, with a tree-lined main street and cute (and hip) shops and boutiques. I guess that’s the main reason I’ve been wanting to visit – I love adorable towns that scream New England. Can’t get enough of them. Even if it’s a town where there’s not necessarily much for my kids to do, if it’s picturesque, I take them with me and find things to do. Which is what I figured would be the case with this visit. But, actually, there was enough to do with my girls, for Ridgefield is a close-knit community with kids all about town. Wherever we went, there were kids walking, running, biking or scooting by. I keep hearing how great the schools in Ridgefield are, so I don’t know why it came as a surprise to see children everywhere. Honestly, it felt like I was on the set of the Truman Show, with kids and white picket fences everywhere, but in a good way. There is a sweetness and a beauty to the town that would make anyone envious of families living there.


We started our afternoon with lunch at Terra Sole, a fancy-ish Italian restaurant with a nice outdoor patio and flowers all around. I thought it would be too upscale to take the girls, but much to our delight, the staff was so kid-friendly and nice, and the food, even more so. The pastas they whipped up were amazing. At $8 a big kids meal that became dinner later on as well, I felt we got our money’s worth. And my chicken Milanese and beet salad, perfection. If a restaurant like this could cater to the girls, I knew we were in kid-friendly territory. Next we went on a shopping and ice cream quest. The girls had brought their allowance money, and were ready to spend. We strolled by some designer shops and Books on the Common book store, and eventually made our way to the incredible ice cream and candy shop, Deborah Ann’s Sweet Shoppe –an old fashioned joint bustling with kids off from school. It is one of those classic places, Americana to the t, and with delicious home-made ice cream and chocolates. The girls were in sugar heaven. Me too. Anyone who knows me knows I love candy, and a good candy shop at that.



We walked down Main Street some more and made our way to the Toy Chest, originally spotted from the car. The girls had their money ready, and had a beanie boo splurge. We seriously had so many beanie boos to contend with when we left, that I told myself they’re never allowed to use that much of their saved up money again. The toy store was a good one though. We kept walking until we hit Ballard Park, a beautiful town park with big, billowing trees, lawns, manicured flowers and greens, and a playground that was under construction (much to the girls’ dismay). But soon we came across Ballard garden, a serene little spot and so darling it felt like something out of the Secret Garden. Wow, really feeling like movies and books in this town! But it was a good find. We walked around, and then made our way back to the car, for the girls were tired.




Ridgefield is famous for more than just being an attractive town – the Aldrich Contemporary Art Museum is here, as well as the Ridgefield Playhouse, both nationally recognized cultural institutions. On our next visit we plan to go to the museum, and hopefully the playhouse for their rendition of the Nutcracker. There is a lot going on in this little town and is worth a visit. You can make a day trip out of it and do some of the cultural things we did not this time around, or combine it with something else. Either way, you will be drawn in by its quaintness and charm. And make sure to drive around the outskirts of town where you will find the beauty of its open space, hills and countryside…we loved Ridgefield!


This article is available as an app through GPSMyCity if you would like to read it offline whenever and wherever. Click here to download the city app, as well as for GPS coordinates of the locations listed.



  1. October 11, 2015 / 1:11 am

    You are killing me ,I will never find time to go to all these grand sights you are presenting. Spoke with my brother today and he suggested when he really retires we should fly us rent a car and see for ourselves the perfect little pieces of heaven you have presented.

    • October 11, 2015 / 5:25 pm

      Ha – love that Jean. Although not everywhere we go is grand. Just nice spots to get away and explore. You know us – we like to see and do everything. As much as we can at least.

  2. October 11, 2015 / 7:01 pm

    Lovely photos. And thanks for a chance to see a part of the world I don’t know at all, and probably won’t get a chance to visit in person.

    • October 12, 2015 / 1:30 pm

      Thanks so much Su. I know – that’s what I love about travel blogging – impossible to go everywhere, so love reading and experiencing through others.

  3. October 12, 2015 / 10:51 am

    Just gorgeous, it really does sound like the most perfect place to live for a family!! I can totally understand why there are all those children around. That candy shop too…. wow.

    • October 12, 2015 / 1:31 pm

      Thanks Joy – I am a sucker for candy shops, and my older age teeth show it uggh!

  4. October 13, 2015 / 4:47 pm

    I really enjoy reading your posts about your surrounding areas – it just looks so gorgeous. And considering we’re planning a big USA road trip to New England hopefully in 2017, this will be added to the list. I can imagine not just driving through Ridgefield… it would be rude not to stop!

    • October 13, 2015 / 5:13 pm

      Love that you’re planning a New England trip! I think you mentioned that before. Well, if you are in the NY/CT area def reach out. There’s too many places to write about, but some “musts”. Happy planning!

  5. October 19, 2015 / 3:52 pm

    Sounds like you had a great day out 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.