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The 203's Town Guide To Fairfield Connecticut

With more and more people looking to trade in their lives in The Big Apple for a highly desired east coast lifestyle, it’s no surprise that Connecticut is on everyone’s radar. (Who knew that CT needed a global pandemic to be put on the map!?!) 

Conveniently located in close proximity to NYC, our home state is filled with charming towns, coastal communities and bustling historic villages that are just as magical to experience as they appear in photographs. 

To help you explore some of our favorite local areas, we’re working on creating ‘Town Guides’ to several of our favorite Connecticut towns & neighborhoods! Whether you’re new to the area, you’ve lived here for years, or you’re simply looking to plan a (covid safe) trip to explore some new spots around the state, our #203TownGuides will give you the inside scoop and everything you need to know to get started!

For our very first #203TownGuide, we couldn’t think of a better place to begin than our home town— Fairfield CT. And when we started planning our town guide to Fairfield, we couldn’t think of a more perfect person to help us with the task. We’ve partnered with our friend and local real estate expert, Cindy Raney, to round up a list of our favorite hometown spots that make Fairfield such a special place.

Before the pandemic, one of Cindy’s favorite things to do with clients moving to the area from out of state was to drive them around, point out her go-to local spots and give them an authentic local tour of their new ‘hood! Because social distancing doesn’t allow her to do that right now, we’re hoping that this Town Guide offers everyone a glimpse of what Fairfield has to offer! 

** Of course, we’re not claiming to list ALL of Fairfield’s Gems (Come on now, that would be impossible)! Below is a list of some of our favorites. If we’re missing something that you think should be on the list, we would LOVE to know in the comments. We will be adding and changing our Town Guides as we go to make sure that eventually, we get 'em all!  **IMAGES, unless otherwise noted are done by one of our photographers, Gina Salvatore. 


We might be biased, but we’re huge Fairfield Fans. Located on the metro north line, Fairfield’s downtown is just over an hour commute to NYC. Over five miles of coastline, pristine hiking trails, endless outdoor activities, a picturesque downtown and a trendy food scene that gives NYC a run for its money-- these are a few of the things that make this community so unique. We love Fairfield for its strong sense of community, laid back vibe and authentic charm. Fairfield has enough personality and culture to win over just about anyone’s heart!



  • Bonda: Delectable upscale menu with a romantic candlelit atmosphere. Bonda is off the beaten trail and certainly a Fairfield gem. We love their excellent hospitality, intimate atmosphere, and that you can reserve a seat at the bar. May we suggest the sriracha fried chicken? 
  • Barcelona Wine Bar: Unique and delicious Tapas with Mediterranean, Spanish, and South American influences. Don't miss the hanger steak!
  • Liana's Trattoria: For a special night, this is our favorite hidden gem of Fairfield. Liana's is off the beaten track, but once you go, you'll be a forever fan. Serving up authentic Italian dishes with exquisite flavors and excellent customer service. Ten out of ten, would recommend.    
  • Centro: Casual date night spot that won’t disappoint. Pro tip- Grab a seat at the back bar.
  • A few more go-to spots: The Grey Goose (a long time go-to of ours. See you there?) & Artisan (Great outdoor patio in the warmer months. Great ambiance. amazing food. Get the sliders!)
  • Brick and Wood: Inspired by Italian street foods & wood-fired pizza, Brick + Wood boasts to offer “old school comfort food wrapped in a contemporary vibe”. Sit by the kitchen to see their chef’s make hand-pulled mozzarella all day long.
  • Molto: High energy restaurant, locally known for their artisanal square brick oven pizzas, fresh mozzarella and home made pastas. May we suggest hitting up Molto on a Monday evening for their half priced bottles of wine? See ya there! #MoltoMonday
  • Colony Pizza: An Irish, dive bar meets… pizza joint? Yepppp!! No menu, no salads, No frills… just pizza (ohh and, beer!). Great for families and totally kid friendly. Famous for their hot oil, thin crust pizza. Our go to order: Hot oil, salad pizza, with extra mozz on top (don’t forget a side of dressing).
  • Sammy's: A southport staple. Classic old school pizza joint with a full menu. Great place to do take out and bring to the beach for a picnic! 
  • Pepe's Pizza: One of CT's most legendary pizza joints has a location right here in Fairfield. Pizza lovers flock to Pepe's for traditional pizza's made in Pepe's coal fired pizza oven. For many pizza fans, Pepe's is the holy grail of ZAA!! (You're going to need to try the White Clam Pizza)


  • Tequila Revolution- Hands down our fave marg in town. Delicious food, great margaritas and a fun, trendy vibe… need we say more?
  • Bodega: Tiny hang out with great eats and an awesome ambiance. We love hitting up Bodega during their Happy Hour on Monday’s!
  • Geronimo:  A great spot for happy hour with friends. Geronimo boasts having the “largest selection of Tequila on the East Coast” so that’s a win for us! Pro Tip: Head there on Tuesday’s for their taco Tuesday special. 


    • Spic & Span: Best deli sandwich around. Spic & Span is a hometown go-to, located in the heart of Southport. We love the iconic old school vibe, the gourmet food options and the excellent customer service. You’ll feel like family the minute you walk through the door. Pro tip- in the summer months, call ahead to place your order!
    • The Pantry: Gourmet pre-made meals, specialty foods and award winning bakery with phenomenal customer service that’s just as impressive as their menu. Their jalapeno popper dip will rock rock your world. **Don't miss the pesto! 
    • Firehouse Deli: We practically grew up on Firehouse sandwiches. Local gathering spot in the heart of downtown (yepp.. they even serve beer!) That one sandwich we can't stop ordering-- The Red Gate, obviously. 
    • The Country Cow: Known by locals as “The Cow” and locally famous for the best damn B.E.Cs around. Pro Tip- Don’t forget to bring cash


    • Shearwater: USDA Certified Organic coffee in The Brick Walk. Definitely a fan favorite around FFLD. 
    • Las Vetas: This funky and eclectic cafe is a Fairfield classic. Grab a coffee on the go or post up here for an afternoon of work (away from home)
    • Sono Baking Company: Grab & go style artisanal coffee shop & bakery in the heart of Southport. **Don't skip the croissants. 
    • Gruel Britannia: Delicious english style cooking with an epic coffee bar. Their traditional english breakfast & bangers are a must try! 
    • Donut Inn: let's just say-- If you know, you know. #LightAndSweet 


      • Be Chocolate: The finest authentic Belgian chocolate shop just popped up in Greenfield Hill (and it’s right next door to Bonda!). Serving small batches of hand crafted chocolates, waffles and hot coco. We love their open kitchen concept-- it’s so much fun to watch the chocolatiers in action!
      • Isabelle et Vincent: Delicious French bakery with the best breads and bakery items in town (in our opinion)!
      • Saugatuck Sweets, Sunny Daes, Milk Craft & 16 Handles: These are all great options for after dinner ice cream (or fro-yo) in downtown. 



      Fairfield town beaches are open to residents in the summer months,  but you can always purchase a day pass if you’re visiting from out of town. *Call Fairfield Parks & Rec for COVID restrictions & up-to-date day pass deets. 

      • Jennings Beach / Penfield Beach: These two beaches are connected, and walking from one to the other makes for a gorgeous beach walk! Both spots have their own parking lots, snack shacks, public restrooms and lifeguards on duty in the summer months. 
      • Sasco Beach: We love Sasco for it’s sprawling views and laid back atmosphere. 
      • Southport Beach: Pull right up to the sand for easy access to your car as you enjoy a beach day. Bathroom available + Lifeguards on duty in the summer months. Beach pass required, but if you ask nicely they are pretty laid back here! :) Pro Tip-- Pack a lunch if your heading there for the day (no food on site).


        • Lake Mohegan: Lake Mohegan & its surrounding open space is made up of 170.4 acres. Dogs are welcome all year and you will find trails for all skill levels. Bring a suit in the summer months and take a dip in the lake! 
        • Brett Woods: Nice and easy hiking, dog friendly! 
        • Devil's Den / Devils Glen: Yea, yea, yeaaaaa... we KNOW it's not technically IN Fairfield. But it's close enough, and totally deserves a shout out. **Definitely don't go cliff jumping.. or else!! :) 
        • Fairfield Theater Company: A fun and vibey center for the arts in the heart of downtown. FTC brings the community together through musicians, actors, artists, writers, fans, and supporters.
        • Fairfield Community Theater: This long time icon of downtown Fairfield is currently being renovated and brought back to life! Locals are excited that the old community theater will be home to Sacred Heart University’s theater program and is set to begin offering performances in the coming months.
        • Live Music in the town green- Seasonal concert series in downtown draws locals to set up yard chairs and picnics-- or to grab an outside seat at one of the nearby restaurants! (May we suggest Centro or Old Post Tavern?) 


        Fairfield is home to a thriving downtown with SO many locally owned boutiques to explore. We love the small business community and checking out what these stores have to offer! We suggest heading into town and bopping around to find the shops you love. (Some of our FAVES- The Perfect Pair, Penfield Collective, Snappy Gator, The BeeHive)

        • Henry Reid- Looking for something extra special? This family owned jeweler is a timeless go-to. Exquisite customer service and gorgeous pieces. Their newly remodeled store is breathtaking! *Our go-to's for anything custom!
        • Looking for 203 Gear? (Heckk yeaa!!) Head to our absolute favorites in downtown FFLD for your 203 goodies :) -- Vintage Garden in the Brick Walk, or No 299 by Firehouse Deli! 

          If you’re looking for more information on moving or relocating to Fairfield, Connecticut contact our go-to local realtor, Cindy Raney & Co, for the best information and honest real estate advice. You will not regret working with this family run business and loyal team. Email- 

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