Destinations North America

Fairfield County, Connecticut Fall Staycation Itinerary

Fairfield County, Connecticut is located in the southwest part of the state. It borders the Long Island Sound. This means there are great beaches but Long Island shields the area from the rough Atlantic Ocean waters. It’s a great place to visit in the fall for so many reasons. Keep reading to see what to do and where to go in Fairfield County.

Where to Stay in Fairfield County

I live in Fairfield County, so I’m going of off recommendations and reviews.

The Westport Inn, in Westport is a great place to stay. This is a recommendation from a wedding I went to. It was the recommended hotel. It’s located on a main route with lots of stores and restaurants.

The Circle Hotel in Fairfield also has good reviews. It’s located near a main route with lots of stores and restaurants. If you love shopping, it’s right across the street from DSW and Marshall’s.

Another place is the Holiday Inn in Bridgeport, which also has really good reviews. Located in the heart of Downtown Bridgeport, you have quick access to the train station, bus station and Long Island ferry. It’s also near the newly opened Bass Pro Shop.

I also recommend the Delamar Hotel, which is in Southport. It’s also received good reviews. Artisan is their in-house restaurant, which features New England-inspired dishes.

What to Do in Fairfield County

Try your hand at apple picking at Silverman’s Farm in Easton. This is a great social-distanced activity for the whole family. Pick-your-own (PYO) is currently only available on weekdays. Their market is open 7 days. Don’t forget to pick up a box of cider donuts. What’s a fall season in New England without cider donuts!

They also sell apple butter, apple pies, apple cider and other New England delicacies. For the kids, or kids at heart, there is an animal farm. They have pumpkins as well, though I’d recommend a different place for dedicated pumpkin activities.

Jones Family Farm is a great place for pumpkin picking. They also have hiking trails and their “corn labyrinth.”

Visit the Captain’s Cove Seaport boardwalk (below). I talked all about this place in a recent blog post. The restaurant closed at the end of September. However the shops are independently run and stay open longer.


Drive down the iconic Merritt Parkway to watch the leaves change colors. Isn’t seeing the changing fall colors one of the main wonders of fall in New England! Marvel at the parkway’s unique bridges, designed by architect George Dunkelberger.

If hiking is your thing, visit the Indian Well State Park. It’s located in Shelton. The coastal location means it has a beach as an added plus.

Note: Due to Covid-19, many farms may alter their schedules or rules. Check with the farm before visiting. Face coverings will be required per Connecticut state guidelines.

Checkout my other Staycation posts here:

St. Mary’s by the Sea- Black Rock

Fairfield Museum and History Center

Seaside Park in Connecticut

Where to Eat in Fairfield County

The Bereket Turkish Grill in Bridgeport has amazing food. Can’t you tell just from the photos alone (below). Its location makes it a little difficult to find. Besides that, it does not disappoint. The packed parking lot every night does not lie.

Bonchon Chicken is located in Fairfield. No more driving all the way to New York or New Jersey to eat this delicious Korean fried chicken. A friend of mine from South Korea recommended this place when he was visiting the States. Every person I’ve recommended it to has recommended it to two more people. It’s just that good!

It’s their double-frying method that leaves the skin so crispy. Your mouth will be on fire (other flavors besides spicy available) but you will keep on eating anyway. Other dishes are available besides fried chicken. See the spicy rice cakes (called Tteokbokki) above, left.

Brewport Brewing Co. in Bridgeport is what the name suggests. It’s a brewery in Bridgeport. They offer their in house beers and unique pizzas. My friends and I like ordering the Meat Master (four types of meat) and the Barrett (Korean BBQ pulled pork). We also choose the build-your-own-pie option a lot. Great root beer available as well. The location has a nice atmosphere as well as plenty of outdoor dining space.


No matter what you choose to do in Fairfield County, Connecticut the options are endless. Plus the close proximity to New York City only adds to all the things you can do!

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