Food Trail #1: Cupcake Trail in Coastal Southwestern Connecticut

| | | |

We are so excited to share the first in a new series for Coast2CoastwithKids: Food Trails. A couple of years ago, we found this great list of ice cream shoppes located in the greater Mystic, Connecticut area. It inspired us to research similar types of themed “tours” through Connecticut; we’ve seen these ideas when researching cities to visit and we wanted to create our own mini versions. Check our CT food trails for chocolate shops, cookies, hot dogs, crepes, tacos, and bakeries.

Due to the ongoing pandemic, and the rise in cases, we have been staying close to home, and mainly outdoors, which has allowed us the time to try hiking (here, here, and here). We think these food trail will be a great way to spend an afternoon (or full day) as a family, try new foods (or new flavors of old favorites), and support local businesses. First up, we’re sharing 8 places to enjoy cupcakes from Norwalk to Fairfield (lower Fairfield County), where all items are homemade daily on premises.

Note: We choose this route (including starting and stop points) for efficiency. There are plenty of additional choices we may have missed, and we plan on adding additional extensions to this route (Greenwich to Norwalk and Fairfield to Milford) in the future- for your benefit, of course 😉

Fairfield Cupcake Trail:

Forever Sweet Bakery in Norwalk ($2.75 for most cupcakes)
We loved the raspberry and chocolate peanut butter cupcakes.
Take home for later: In addition to cupcakes, the bakery also makes beautiful cakes, cake pops, and sugar cookies
Noteworthy: The shop is closed on Sunday and Monday; grab and go only (no place to sit); large parking lot in a plaza with other shops.

The Sono Baking Company & Cafe in South Norwalk ($3 for small cupcakes)
We loved the red velvet cupcake (available everyday)
Take home for later: Over a dozen types of bread, quiches, desserts and pastries galore. I would literally eat every.single.thing they make.
Other locations: Darien and Southport
Noteworthy: All locations are closed on Mondays, and close at 3pm Tuesday- Sunday; the SoNo location offers a great menu of breakfast and lunch options (it’s one of my favorite places ever for both meals!); there are a few tables inside for smaller sized parties; restroom facilities available; parking lot (SoNo Square) around the corner

The Cake Box in Westport ($3.25/ cupcake)
We loved the hot cocoa and sweet & salty cupcakes
Take home for later: Every other flavor. The shop only sells cupcakes, which are made each day at the Ridgefield location and hand delivered to the Westport shop.
Other location: Ridgefield
Noteworthy: Westport location is closed Sunday, Monday, and Tuesday; both locations open at 11am; limited parking in front (larger lot across the street); very large selection of gluten free options (for the same price!); grab and go, with a few chairs outside.

Isabelle et Vincent in Fairfield ($2.25/macaroon)
We loved the macaroons- over a dozen varieties. Cupcakes are special order only.
Take home for later: Homemade French baguettes and an incredible list of breads, pastries, and coffee
Noteworthy: Open seven days a week; parking lot right in front; great ambience with space to sit indoors

The Pantry in Fairfield ($3/cupcake)
We loved the apple cupcakes and the sprinkle vanilla cupcakes
Take home for later: key lime pie (their most popular item) and World Peace cookies. 
Noteworthy: Open seven days a week; parking lot right in front; a couple of tables both inside and outside for eating. The Pantry is one of my favorite places for catering and for lunch. In addition to the bakery, they have a full service deli, salad bar, prepared foods and freezer section, and small grocery store with tons of gourmet options. Their catering menu is amazing- we ordered sides for Thanksgiving and Christmas and devoured everything.

Chaves Bakery & Deli in Fairfield ($1-$2.35/cupcake)
We loved the traditional flavors (chocolate and vanilla) and rose applique 
Take home for later: chocolate peanut butter squares and Portugese rolls and breads
Other location: State Street in Bridgeport
Noteworthy: Open seven days a week; parking lot right in front; restroom facilities available; wide selection of bread, rolls, muffins, cakes, and coffee; grab and go only

Billy’s Bakery in Fairfield ($2/cupcake)
We loved the chocolate cupcakes
Take home for later: pies, quiche, and cookies
Noteworthy: Closes at 2pm on Sunday; parking lot in front; full deli and wide variety of bagels, breads, quiches, and a variety of coffees. There is an outdoor patio with tables and chairs, and one table for indoor dining. 

Alina’s Cakes and Cookies in Fairfield
We loved the cannoli, smores, and caramel cream cupcakes
Take home for later: every other flavor, chocolate covered pretzels, cookies, and made to order cakes.
Noteworthy: The shop closes at 1pm on Sunday; it’s part of a large plaza of shops with plenty of parking in front; grab and go only- no place to sit.

Other sources for “research”: Three of our favorite sources for researching anything Connecticut related are (the official state tourism website), (THE resource on all things food related), and (a magazine I have subscribed to for years, full of info on a great variety of topics)

For more fun in Connecticut, check out our list of 30 places we love and 32 places where we love to eat in Connecticut, and places to hike here and here.  And follow along on our adventures on Instagram, Facebook, Twitter, and Pinterest.

Similar Posts


  1. A fantastic idea for families to spend some time together and enjoying treats in the process! This is a fun and great way to learn more about your towns, and have family fun time while enjoying some very tasty.

  2. Great job as usual! I have already been to Alina’s and definitely try out their cookies and cream with an Oreo on top. So good!

  3. amazing cupcakes! such a nice family bonding that kids will definitely enjoy because of food 🙂

  4. amazing cupcakes! such a nice family bonding that kids will definitely enjoy because of food 🙂

Leave a Reply

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