I have photographed several families while they were vacationing in Westbrook and Old Saybrook, CT. Sometimes, these families have asked me for recommendations for places to eat, and ideas for fun things to do while they are here. I thought it would be fun to make a blog post suggesting things to do while on vacation in Westbrook, Old Saybrook, and anywhere else up and down the CT Shoreline.

*I have lived on the CT shoreline for many years, so keep in mind that these are all my own opinions and favorites! Besides the many great restaurants, there is so much to do and see. There is fantastic outlet shopping and local shops, art, music, and local attractions.

Some Of My Favorite Places To Eat:

I photographed a family on vacation at Water’s Edge in Westbrook, CT. When we were done with our session they asked me where they could get some good pizza, and some good Chinese food.

For Pizza, my favorite place is Otto’s in Chester. Oh my goodness, their pizza is amazing. For a more local Italian you can’t beat Alforno’s in Old Saybrook. We love this place. Their veal ricotta meatballs are amazing!

For Chinese food, the place to go is Hong Kong in Essex.

Another place I love is Bill’s Seafood in Westbrook. A casual place with great seafood, they have a fun “tiki bar” outside that often has live music. This place is located right next to Westbrook’s Singing Bridge. For the BEST lobster rolls on the shoreline (in my opinion) is none other than Westbook’s Lobster Landing. YUM!

And for a couple of kid-friendly places, check out Pizzaworks in Old Saybrook, and for “burgers, wings and things” there’s Jack Rabbits in downtown Old Saybrook.

Shopping:

There is some great outlet shopping, both in Westbrook at The Westbrook Outlets and my personal favorite Clinton Crossing in Clinton. I’ve had clients go shopping there to get their outfits before their family photo session while they were here on vacation!

For more local shopping, downtown Old Saybrook is adorable with its little gift shops. Also, be sure to check out The Pink Sleigh in Westbrook for all kinds of Christmas and holiday gifts in an enchanting little barn. I believe they open mid-summer so be sure to call first. This place is definitely worth a visit!

Other Local Attractions:

For things to do with the kids there’s Essex Steam Train in Essex, and Mystic Seaport & Aquarium in Mystic. I highly recommend both those fantastic places!

And for the grown-ups, I recommend Chamard Vineyards in Clinton. This is a beautiful local farm, winery, and bistro with breathtaking grounds open to the public. We love this place!

If you’re looking for music, Old Saybrook offers live summer concerts on the green with some good music! It’s always fun to bring a blanket and appetizers to enjoy a beautiful summer evening while you’re on vacation.

We also love The Kate in downtown Old Saybrook for its fantastic concerts and musicals, as well as The Ivoryton Playhouse in quaint downtown Ivoryton. We have been to both these places many times and I recommend both as things to do while on vacation on the CT shoreline.

And of course, while you’re on vacation, please get some professional family photos!

Here’s Why: As a photographer, of course I recommend this, but for very good reason. Your whole family is here on vacation, together, relaxed and happy. If ever there was a perfect time, it’s this. At some point over the years, you’ve probably already thought you should have family photos done, am I right? So, I promise make it easy for you, by helping to determine the perfect location, and offering suggestions on what to wear. I have done many photo sessions when families are here on vacation, and it’s always a wonderful keepsake to remember your time together as a family.

I hope you enjoyed all my suggestions for things to do while on vacation along the CT Shoreline! Hope to see you soon. 🙂

To get in touch with me about a session of your own, click below. I’d love to chat!

Linda Sobolewski is an on-location, natural-light, professional photographer specializing in seniors, baby, family & children photography.

Linda Sobolewski Photography is based out of Old Saybrook, CT and serves the Connecticut shoreline and surrounding areas.

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