Connecticut Trip Review

Our first vacation as a family of three was a short weekend trip to the Connecticut coast. Jay needed to travel to Bridgeport for a work seminar, so we decided Connor and I would come along. Our itinerary called for two nights near Bridgeport and one near New Haven. We didn’t pack our days with activities, so we enjoyed a relaxing getaway!

Day 1 – Setting Off

We set off on our road trip just after lunch with hopes of avoiding rush hour traffic in the evening. Along the way, I wanted to stop at Stew Leonard’s, an interesting grocery store in Connecticut. It’s a great place to stop and pick up vacation snacks, especially if you have kids! The store is full of animatronic animals and displays to entertain youngins (or older folks like me).

Once we made it to the hotel in Milford, we searched around for dinner. Downtown Milford has a nice green space and a block of restaurants to choose from. We ended up at Eli’s Tavern and enjoyed our apps, dinner and drinks. I wasn’t too impressed with my lobster roll, but I guess I shouldn’t have expected Maine standards.

Day 2 – Milford

Connor and I dropped Jay off at his seminar in the morning then set out on our own adventure. Silver Sands State Park was the first stop for a long walk by the ocean. There’s a new boardwalk running along the coast that was perfect for walking with a stroller. I loved smelling the salty air and enjoying the view while listening to my audiobook.

For lunch, I scoped out any nearby restaurants ahead of time and found a small Greek cafe. Luckily, it was within walking distance of the one end of the boardwalk. They had a decent sized menu with plenty of sandwiches and salads for lunch.

After eating, we still had some time to kill so I looked up local bookstores, naturally! Penny’s Bookshelf popped up on Google. It seemed a little run down from the outside but indoors was a book lover’s delight! Although the store is small, it’s absolutely packed with books. Pricing is generally half of the original sales price, with nothing more than $8. I snagged two paperbacks from Louise Penny’s Inspector Gamache series for $7 each.

By that time, we made our way back to Jay’s seminar to wait for him to wrap up. It ended up taking a bit longer than expected so I read for a bit in the car then joined Connor in napping 🙂

For dinner, we stopped at Windmill Tavern. It doesn’t look like much, but inside we found a typical pub type restaurant and delicious food! I also wanted to stop by a local ice cream place, Walnut Beach Creamery, but sadly it was only open on weekends until Memorial Day. We were one day too early!!

Day 3 – New Haven

After Jay returned from a quick work project in the morning, we packed up and headed north to New Haven. My goal was to stroll around Yale University’s campus. Who knows, maybe Connor would catch the bug and end up here someday! I wasn’t expecting the buildings to be sprawled throughout the city though. While it’s undeniably pretty, I wasn’t a fan of the traffic whizzing past constantly. We meandered about for a bit and grabbed a quick lunch from a cafe. You can take a student lead tour of the campus, which I’m sure is full of fascinating information. However, we decided to forego that since we had Connor and the stroller.

Our hotel was a bit further up 95 in Branford so we stopped there to check in before heading out again to a local brewery. It was a gorgeous day and I wanted to enjoy the sunshine. Stony Creek Brewery was the perfect option! It has a gorgeous deck that looks over the water as well as a lower level full of additional seating and games right along the water. While Connor slept (he misses all the fun!) Jay and I enjoyed our drinks and the weather.

Since pizza Friday is a tradition in our family, we just decided to order takeout from the pizza place right next to our hotel and eat in our room. We don’t have cable so it’s always a treat when we can watch regular TV at a hotel haha.

I also begged Jay to go back out afterward for a second try at ice cream. Ashley’s Ice Cream is a local ice cream shop with a huge variety of flavors…and it was open!! I ordered a delicious (but expensive) waffle cone with Nutella Chip and Heath bar ice cream. Yummmm. It’s located on the town green so it would have been a beautiful place to sit and enjoy if we weren’t so tired. Life with an infant…

Day 4 – Trader Joe’s

My two requests for our final day were a walk and Trader Joe’s. Thankfully it was another gorgeous day, so I navigated to Bradley Point Park, south of New Haven. There’s a small charge to park for nonresidents, but the pathway along the coast is worth the $1.50 per hour. It’s paved, so it was easy going for the stroller. We walked for almost an hour enjoying the views.

Next stop was Trader Joe’s!! When I lived in New Jersey, I spoiled myself with trips to this unique grocery store. Their store brand products are delicious and fairly inexpensive. It should be no surprise that two grocery stores were the highlights of my trip 🙂

Memorial Day weekend traffic made our drive home from Connecticut longer than usual, but we made it safe and sound. Thankfully, our first trip with a baby was a success!! Here’s to many more in the future.


  1. Ah my home state! Where do you live normally?

    Stew Leonard’s has the best ice cream, popcorn, and cider donuts. AMAZING. I’ve been meaning to check out that beach – I’ll have to this summer.

    Yale is a weird campus – there’s a nice section that’s very secluded and wooded (I think where the library is) but otherwise it’s very odd haha.

    AND TRADER JOE’S my other favorite place!!

    1. We live in PA, so only a few hours away. I was eyeing up the cider donuts but passed : / Good to know for next time! I can’t leave Trader Joe’s without at least one or two jars of cookie butter. Absolute staple.

  2. Stew Leonard’s sounds really fun–just the sort of simple, random place I like stumbling across while traveling! You had some nice strolls by the water–I love spending time close to the sea!

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