10 Family Friendly Hiking Spots in Fairfield County, Connecticut

We’re back with another index of places we’ve explored in the past year. (We’ve previously posted about places to hike in Western Connecticut and places to hike in the Mystic area.) Many of these spots are practically in our backyard and it’s taken us an embarrassingly long time to check them out. They are all free to visit in the off season (October-May), although some locations do rely on donations for upkeep and programming. Most of the locations in this collection are somewhat of a stretch for “hiking” for true hikers, as many of the trails are under three miles and fairly easy to navigate. But we think they’re all great spots for family fun, especially families with younger kids.

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Food Trail #7: Bakeries in Milford, Connecticut

Milford, Connecticut, a small city located on the edge of New Haven County along the Coastal Connecticut I95 corridor, is home to over a dozen named beaches (5 are open to the public), a state park, great shopping and restaurant hubs, and plenty of yummy bakeries. For our seventh food trail (check out #1, #2, #3, #4, #5, and #6), we started on the south side and made our way north, stopping at seven bakeries serving up plenty of homemade pastries, desserts, salads, sandwiches, full meals, and drinks. Here are our top picks:

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Food Trail #6: Tacos in Stamford, Connecticut

This week, we’re sharing a loop we’ve made throughout parts of Stamford, Connecticut that features 7 great spots for tacos. Full disclosure: There are some additional spots for tacos we did not try: Tomatillo Taco Joint opens at 3pm on weekends and Ole Mole was a bit far off our loop. (close to the Merritt Parkway). Stamford has dozens restaurants and we hope to return soon to explore more locations. Every person we met at each of the following spots was warm, inviting, and enthusiastic about their passion for making good tacos. Truth be told, we loved them all! Note: Call ahead to check current pandemic restrictions regarding indoor dining versus takeout/delivery options. While we ordered take out at each location, many of these locations are offering safe options for indoor dining.

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Food Trail #5: Crepes Trail in Norwalk, Connecticut

This week’s food trail is compact- we’re staying super local in one city: Norwalk, Connecticut. Norwalk offers plenty of family friendly places: Stepping Stones Museum for Children and Maritime Aquarium at Norwalk are two museums for which we had a family member for YEARS when our children were younger. We visited either spot at least once a week. Norwalk boasts several beaches and parks, boat cruises, and tons of shopping areas, including the SoNo Collection, an upscale mall that just opened in 2019. There are also dozens of restaurants in both the main city and the area known as “SoNo” (South Norwalk) which is extremely walkable. We’ve been going to SoNo for years to meet up with friends from the City (aka NYC) and friends who live in Westchester County.

This week’ we’re sharing some of our favorite restaurants throughout Norwalk, all of which make delicious crepes.

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Food Trail #4: Hot Dog Trail from Fairfield to Milford, Connecticut

We’re back with our 4th food trail throughout parts of Connecticut. In the past month, we have created a cupcake trail from Norwalk to Fairfield, a chocolate shop loop from Westport to Bethel and back to Fairfield, and a cookie trail from Branford to Old Saybrook. This time, we’re checking out some of the top rated hot dog spots from Fairfield to Milford. As always, there are so many great spots and we had to set the limit at ten, so don’t take this as a comprehensive list! Many of these spots are casual restaurants, with very tight parking lots, limited indoor dining, and no public restrooms. While they stay open all year, they mainly have outdoor picnic tables for dining. We’ve noted the spots that have indoor seating and restroom facilities. But we guarantee what they lack in size, they MORE than make up for in friendly staff and really good food!

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Food Trail #3: Cookie Trail in Coastal Central Connecticut

We’re back with our 3rd Connecticut Food Trail (see the cupcake trail here and the chocolate shop trail here). We’re staying local this winter, due to the pandemic, and it’s turned out to be a great time to explore many local bakeries and restaurants. While we know there are hundreds of great spots throughout the Nutmeg state, we’ve researched bakeries near one another and created a trail that would be a fun way to spend an afternoon or whole day.

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