Fairfield is located right on Long Island Sound and has some lovely beaches to offer. The Circle Hotel is a 1-mile walk from Jennings Beach, while the Inn at Fairfield Beach is just steps from a private hotel beach or a 7-minute walk from the popular Penfield Beach. We also highly recommend the arguably more chill Southport and Sasco beaches. Please be aware that you cannot park at any of the town beaches or nearby streets without a resident sticker (unless you want to spend $50 for parking!). If you want to visit the beaches, we recommend staying at one of those two hotels, or plan on taking a taxi or Uber to the beach.
One of our favorite places to hike in town! (Also the location of our second date!) Parking at the lake in summertime might require a resident sticker, but if not, there are some trails off of the lake parking lot. However, we recommend continuing up Morehouse Highway alongside the lake until you reach a dirt driveway and another parking lot. Here you will find the Cascades, a beautiful trail system complete with lots of dogs to pet, beautiful waterfalls, and some not-entirely-legal swimming holes!
The perfect spot for a short and sweet hike. We used to frequent this spot in our Fairfield days. Go straight for the pond and the "best tree in town" or go right for some beautiful creek views.
One of our all-time favorite restaurants. Their margaritas are ridiculous.
We aren't sure how Fairfield got so lucky to end up with this ridiculously hip ice cream spot. Strawberry and Balsamic sounds weird, but it's not. A must for all you Instagrammers.
A more traditional ice cream, Sunny Daes is the best of the best. There is another location on the post road near the Circle Hotel.
If you grew up in Fairfield, you probably ate bacon, egg & cheeses from Country Cow on a regular basis. Get the full Fairfield experience by picking up one of these beauties.
Connecticut and New York are famous for having the best pizza in the world. Sorry, Italy. Nauti Dolphin is arguably the best in Fairfield.
Duchess is a fast food chain that is exclusive to Connecticut, and the most top-notch fast food we've ever had. Jeff recommends the hot dogs, but everything is great!
This neighborhood is home to lots of fun bars and amazing restaurants. Some favorites include Tautog Tavern, BRYAC, Walrus + Carpenter, TRU North, Brennan's Shabeen, and Timothy's Ice Cream. Take a drive or a stroll around Saint Mary's and check out the views of Long Island Sound.