Food Trails


While the COVID pandemic has put a damper on many plans to travel extensively in 2020 and 2021, the restrictions have given my family a few silver linings; two of the most significant benefits have been the opportunity for more time together as a family and the gift of time to explore our greater Connecticut “backyard.” We’ve been lucky to discover and rediscover so many family-friendly places through Connecticut. 

According to the Connecticut Restaurant Association, there were over 7,800 restaurants and bars throughout the state in 2017. Most restaurants now offer take-out and curbside delivery, making it convenient to enjoy meals on the go or at home safely. When our family read about the struggle many restaurants face with a sharp decrease in patronage, we decided to order take out an additional night each week. 

A craving for cupcakes and a request for recommendations on social media led to an enormous list of bakeries in the area. In the name of “research,” we decided the best option was to choose two cupcakes from each bakery, bring them all home, and spend the next week sampling them all. We had so much fun with cupcakes, and we started creating other trails.

Here are six trails your family might enjoy:

  1. The cupcake trail from Norwalk to Fairfield was our very first trail. We found eight bakeries that featured cupcakes. We asked for recommendations and most popular flavors from the bakers, and then added one or two cupcakes that looked unique or original to that bakery. We feasted for an entire week on cupcakes each night for dessert.
  2. Chocolate shop loop from Westport to Brookfield to Fairfield. This trail made a loop around a larger portion of Fairfield County. Most of these shops specialize in handmade truffles and other chocolate delicacies. Many of them also sell other popular candies and sweet treats. We asked shop owners for their most popular chocolate flavor and one unique chocolate and usually added one or two additional items. Many shops sell chocolates in sets, but some will allow guests to purchase chocolates individually. Keep the chocolates in the fridge, and they will stay fresh for a few weeks (if you’re that disciplined).
  3. Cookie trail from Branford to Old Saybrook. We usually drive past the coastal central part of the state and are so glad we made time to explore! Many of the bakeries we visited are located near the town greens, which are perfect spots for picnics, and offer various sweet treats. Cookies freeze well, so there is no need to rush to eat them all in one day.
  4. Hot dog trail from Fairfield to Milford. We had to pace ourselves with this tour, as hot dogs don’t save well. We chose one hot dog with different toppings at each spot and saved room for one additional pairing, like fries, onion rings, and milkshakes. Most of these spots are all quintessential hot dog stands- the ambiance may not be fancy, but they sure know how to make a great-tasting hot dog.
  5. Crepes trail in Norwalk. We couldn’t believe how many restaurants in Norwalk create a variety of both sweet and savory crepes. We took them to go (ice cream aside, they actually travel very well!). All five restaurants have ample indoor and outdoor dining space.
  6. Taco trail throughout Stamford. It was hard to narrow down the numerous restaurants that serve delicious tacos, but we found seven spots in Stamford’s two main areas that made the trail quick. We’re not usually adventurous when it comes to tacos (choosing the same beef, chicken, and shrimp fillings), but we experimented more on this trail and even found a s’mores taco with a cereal shell and ice cream filling!

Creating your own food trail is a great family activity. Pick a favorite family food (ice cream, milkshakes, and donuts are all on our future-trail list) and have the kids research locations. Three great websites for research are,, and Have the kids map out a route on google maps. Be sure to confirm hours of operation and peruse the menu for unique flavors or takes on the featured item. 

Jenn Record, a Fairfield County high school English teacher, is the founder of the family travel blog Along with her husband and two children, she enjoys road-tripping and exploring the country via national parks, historical, art, science museums, presidential libraries, baseball parks, and wherever the locals are eating.


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