Known as ‘A Small City with a Big Heart,’ Milford, located at the Southern tip of New Haven County, offers small town charm with plenty of New England-style appeal.

Because our grown children and their families all live in different states, we’ve made it a priority to do a vacation with them all every other year. We’d love to do it every year, but we need to honor the fact that they don’t have as much vacation time as we do yet.

In 2023, we chose the small town of Milford Gulf Beach, Milford, Connecticut. We stayed for the Fourth of July week and it proved to be an excellent choice.

Where to Stay

Airbnb in Gulf Beach, Milford, CT

There was a total of nine of us staying in this Airbnb, including three children ages three, eighteen months, and six weeks old. This particular home was perfect for our needs. The kitchen was extensive with two ovens, one gas and one electric, two full-size refrigerators, along with plenty of counter space and dishware. The house has four bedrooms and four bathrooms, so each family had their own. There were also two spacious living rooms where we all fit comfortably. Furthermore, the yard was large and well maintained with a fun bocce ball court that we all enjoyed.


The only issues in terms of “kid friendly-ness” was the valuable instruments that were all around the house and the cacti that are right at child height. You’ll want to keep an eye on little ones so they don’t learn about the sharp points of cacti the hard way or break anything important. But all in all, the home worked out great for us!


Now for the good stuff. There are a lot of fun things to do in Gulf Beach!

What to Do


Eisenhower Park: This park has several trails that wind through wooded areas, offering a peaceful and picturesque hiking experience; it’s three miles on flat terrain. There’s a big bug-themed letterboxing trail that’s perfect for kids. Plus, it has a small waterpark and splash pad! The park also includes Bodie’s Place, a playground especially designed to accommodate children of all abilities, with sensory activities, oversized structures, along with plenty of ramps and plenty of open spaces. (A stroller-friendly bonus!) 

Walnut Beach Playground: This playground is near Walnut Beach in Milford, and it has climbing structures, swings, and slides suitable for young children. It’s a great place for the little ones to burn off some energy.


Miford Gulf Beach: Have a Beach Day building sandcastles, collecting seashells, playing in the water, chasing seagulls, taking a stroll along the boardwalk, and possibly exploring small marine life in the shallow tide pools. The sand is a bit rocky, but the kids didn’t seem to mind and had a blast exploring.


Silver Sands State Park Boardwalk: Located adjacent to Milford Gulf Beach, this area is known for its sandy beach and dunes. The Silver Sands State Park offers a beautiful boardwalk trail along the coast. (Unfortunately no doggies allowed on the boardwalk.) It’s a scenic walk with stunning views of the Long Island Sound.

Beardsley Zoo, CT

Beardsley Zoo: Located in nearby Bridgeport, Beardsley Zoo is a popular destination for families. It’s the only zoo in Connecticut and houses a variety of animals, including tigers, wolves, monkeys, and more. The prairie dog exhibit was especially fun because kids have an opportunity to poke their heads up through these clear plastic viewing portals that allow them to get up close and personal with the prairie dogs. It’s a small zoo, so don’t expect the same level that you would find in a big city. But for a really young children it’s a great first zoo experience. The zoo also offers educational programs and interactive exhibits.


Downtown Milford: The historic downtown area of Milford is worth exploring, with its charming streets, boutique shops, art galleries, and a variety of restaurants. Take a stroll, grab a bite to eat, and enjoy the ambiance of this quaint coastal town. (Don’t forget to stop by Scratch Baking. You won’t regret it!)


Milford Harbor: Located in the heart of Milford, the harbor offers beautiful views of the water, boats, and a scenic marina. You can take a leisurely walk along the waterfront, watch the sailboats, or enjoy a meal at one of the waterfront restaurants.


Hotchkiss Bridge: From the center of the Hotchkiss Bridge looking north, there is a beautiful view of the arch under the Memorial Bridge that frames the waterfall.


Coastal Center at Milford Point: This is great for anyone interested in birdwatching. You can walk along the shore through the marshland. Plus, there’s a building with small aquariums in several observation decks that look over the marsh and the Housatonic River, They also offer guided canoe tours through the local Audubon society, however the youngest passengers must be at least eight years old.


PEZ Visitor Center: Located in nearby Orange, just a short drive from Milford. It’s a fun and interactive museum dedicated to the iconic PEZ candy and dispensers. You can learn about the history of PEZ (!!! How cool is that?! Ha ha!), and see the world’s largest PEZ dispenser. Everyone gets a scavenger hunt/Bingo card upon arrival, and you (the parents unless you have older kids) have to hunt around to find specific Pez dispensers from throughout history to win prizes (Pez dispensers full of Pez candies). The kids had a blast in here – mostly because they came out with a treasure trove of Pez! (You pretty much make up the cost of your tickets in Pez.)


Mondo Ponds Nature Preserve: This 36-acre nature preserve is located a short distance from Milford Gulf Beach and offers various trails that wind through ponds, wetlands, and wooded areas. It’s a great spot for a family hike and observing local waterfowl and wildlife. Fishing from shore is permitted.


Charles Island: Located just off the coast of Milford, Charles Island is a popular destination for nature lovers and beachgoers. It’s accessible by a sandbar during low tide and offers beautiful views, walking trails, and the opportunity to explore its natural habitats.


Barnum Museum: Situated in nearby Bridgeport, the Barnum Museum is dedicated to the life and legacy of P.T. Barnum, the famous showman and entrepreneur. The museum showcases artifacts, exhibits, and displays related to Barnum’s career and the history of circus entertainment.


Downtown Milford’s Farmer’s Market: Open Saturdays, 8:30 a.m. – 12:30 p.m., summer through fall. You can pick up fresh fruits and vegetables straight from the farms that grew them, as well as prepared foods, home goods and gifts.


Barnes & Noble: If you’re looking for a little rainy day fund to do with kids, or just because you love books, this store offers a Saturday Storytime in the kid’s department, each week at 11:00 a.m.


Jesse’s Toys: This super-fun shop is located in the nearby town of Orange. The shop is the epitome of what a toy store should be. It is incredibly well organized and the owners really know their stuff for entertaining infants to big kids. The shop itself is charming and extremely well organized. Gigi and Grandpa had a lot of fun bringing the grandkids there, letting them take it all in, and then telling them they get to choose whatever toy they wanted. Because, of course, it’s the grandparents job to spoil the grandkids, isn’t it? 😉


Yale University: Approximately 15 miles from Milford, you can explore the renowned Yale University campus. Stroll through the beautiful courtyards, buy Yale T-shirts, and have fun pretending you went there.


Thimble Islands: Embark on a boat tour from nearby Stony Creek and explore the scenic Thimble Islands. These small, rocky islands are known for their natural beauty and charming waterfront homes. The boat tours offer insights into the history and ecology of the area.

Where to Dine

We prepared most of our meals at the Airbnb, but there are some local establishments worth mentioning.

Walnut Beach Coffee House: This place is cute, cozy, and close to beach, with a surprising amount of tables and comfy chairs for seating. They serve fair trade coffee along with fresh-made bakery items, paninis, wraps, and salads. And they also have a nice kid-friendly section with books and stuffed animals.

Café Atlantique: A bit cramped to sit indoors, but there’s outdoor seating on lawn, and live music on weekend evenings. In addition to an extensive coffee menu, they offer delicious breakfast and lunch options ranging from eggs to lox, paninis, and a variety of crepes. They serve cocktails too! Monday through Thursday after 4pm you can enjoy a free glass of house wine with the order of any entrée. For tea lovers, they have multiple chai tea latte options including lavender.

Stonebridge Restaurant

This place is in a beautiful setting and offers five unique dining spaces. For indoor seating, there’s a main dining room with an inviting fireplace and bar, and a cozy pub room that’s more casual. For those seeking alfresco dining there’s a garden setting, as well as a deck and patio overlooking the Wepawaug River with its sparkling waterfall.

We took all the kiddos and sat on the deck, and it was an excellent choice. The ducks paddling in the river and the numerous trains that go by provided endless entertainment for the youngest members of our group. They have an extensive menu with everything from seafood to steaks, as well as kid-friendly and gluten-free options. And their Parmesan truffle fries are da’ bomb!

Scratch Baking

This is an absolute not-to-be-missed experience. Everything is baked fresh from scratch every day, and their pastry selection is awesome. The service is excellent. They have a number of gluten-free options as well and they were all absolutely delicious! I can’t recommend this place highly enough!

Greek Spot Café & Grill

True confessions: We didn’t try this place, but if you’re looking for a quick, casual dinner option, this restaurant is alleged to have best carryout food in the city.


New Haven, CT Apizza

When you stay in Milford, you’re right next door to the town of New Haven, which is renowned for its pizza, or rather “apizza.” You have to try it! The name pays homage to the language spoken by Neapolitan immigrants who introduced pizza to the area. New Haven-style pizza is known for its thin, chewy crust. It’s traditionally baked in a coal-fired brick oven, giving the crust a sooty, smoky flavor and a characteristically charred quality.  You have to try it!


Frank Pepe’s

Frank Pepe’s opened in 1925 and their “original tomato pie” is a New Haven pizza legend. But be warned, there is no mozzarella, or “mootz” as they call it, on the tomato pie. Instead you’ll find a blend of strong Parmesan baked in with the tasty sauce. Other signature plies include their meatball and ricotta, chicken diavolo, and a white clam pie.


Modern Apizza – NEED PIC!

Modern first opened in 1934, and it’s the second oldest apizza place in New Haven. This place definitely does not skimp on the toppings. Try the Italian bomb, a pie loaded up with hefty chunks of Italian sausage, bacon, pepperoni, onions, peppers, mushrooms, and garlic, along with a gooey blend of mozzarella and Romano cheeses.  And it was delicious!


Sally’s Apizza

Sally’s is right up the street from Frank’s, and it opened in 1938. You’ll often find a long line waiting for tables before noon. They serve the New Haven Original Clam Pie, one of the best in the area, with briny, tender bivalves, a healthy dose of garlic, and savory mozzarella. You can skip the line for eating inside and simply order from a takeout window. Then you can take it to enjoy it a little nearby park that has a picnic table.



Opening in 1996, this apizza joint is a relative newbie, and it clearly caters to the nearby Yale University crowd. There’s a pool table, a variety of beers on tap, and dancing at night. They claim to have the thinnest crust in the city, and people unanimously recommend the Mashed Potato and Bacon pizza. It’s exceptional with light, fluffy potatoes, crispy bacon, and a robust blend of Parmesan and garlic that gives the whole pie a satisfying boost of flavor.


What’s a summer vacation without ice cream for dinner once in a while, right? I proposed that we do an ice cream taste test to see which of these was the best. But each place is unique and their ice cream options are creamy and delicious.


Scoopy Doo’s Ice Cream & Sweet Shop

this place is located right near Milford Gulf Beach, and it’s a local favorite. They offer lots of ice cream and soft-serve options in a wide variety of flavors, including lemon/blueberry cheesecake and honey lavender. You can get fresh-made waffle cones, sundaes, milkshakes, and more. If you order a toddler cone, they put adorable little eyes on the ice cream which the kids love. The line can get long but it’s worth the wait.


Walnut Beach Creamery

Situated near Walnut Beach in Milford, Walnut Beach Creamery is known for its homemade ice cream crafted with fresh ingredients. They have a rotating selection of flavors, including classics and unique creations; everything from Cinnamon Toast to Chocolate Chili to Peanut Butter Ice cream. They also offer vegan and dairy-free options.


The Sundae House

This family owned and operated establishment has been serving guests since 1963. Their ice cream menu is extensive including hard-scooped and soft-serve flavors. They offer the best upside down banana split in town, made with vanilla chocolate swirl ice cream, pineapples, cherries, and chopped banana. And then the whole confection is doused with a generous amount of chocolate syrup and topped with whipped cream and a cherry. Yum!

Helpful Tips

  1. Our grandkids were young when we made this trip, ages three, 18 months, and six weeks old. To help add to the fun of the week, and reduce the number of things our adult kids needed to bring along, Gigi and Grandpa brought little surprises that the older kids could unwrap each day and use for play time.
  • Water/sand toys; including buckets and sponges
  • Craft supplies: markers, crayons, paper, and stickers
  • Books for story time
  • A nature scavenger hunt along the beach for seashells, rocks, feathers, leaves, piece of seaweed, and a small bucket to collect their treasures
  • Beach ball for a game to keep it in the air; or bring plastic bottles as pins for bowling
  • Paints, brushes (and glitter if you’re really brave) for shell or rock painting activity
  • Bubbles!
  • A blowup pool. We gave that gift to the six-week-old and mentioned that he was sharing it with the older cousins. This helped engender warm, fuzzy feelings toward their new cousin baby cousin. Adorable!


  1. For these multifamily vacations, Gigi and Grandpa pay for the Airbnb. But each family pays their own way to get to the location. And for meals, each family takes responsibility for a dinner or two. But everyone is on their own for providing breakfast and lunch food for their individual families. (Of course, there are exceptions, such as when Gigi and Grandpa bought treats for everyone from Scratch Baking…multiple times. But by dividing the main meals up this way, it keeps the whole food situation simple and easy to manage.


  1. To break up the childcare duties and give everyone some adult time, the men or the ladies can spend bonding time going to a coffee shop, nail salon, golfing, etc. while the other group watches the kids. Then flip it around so everyone gets a break!
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