Old Saybrook, CT

Old Saybrook is a small, proud community and one of the most charming towns you’ll ever come across. Hundreds of years of history are engraved into the backbone of our Main Street. We have beaches, golf courses, town cookouts, parades, and a nature preserve. All that doesn’t compare to the people. I’ve only lived here a short while, and the fact that it feels like I grew up here speaks more than any story I can share about the town.

Stories About Old Saybrook

On a hot summer day I was telling the local barber how my wife was eight months pregnant and our new home didn’t have AC (of course). And this time of year when it’s so hot, AC units are always sold out…that same day he and his wife showed up at our home with three extra units! I offered to pay him, but he just said to pay it forward.

After a storm our elderly neighbor had a tree down on her power lines. She was home alone without power, and parts of her driveway were blocked. I texted my electrician if he knew anyone at the power company that could be of help faster than the overwhelmed power company. He came over immediately and restored her power. Turns out his son had a tree company and they cleaned everything up that day at no charge! These trees were huge!

Our first week in the new neighborhood, all our neighbors came up to our front door to introduce themselves. Some brought food, others wanted to just say hi. Coming from an urban condo, we were like, “Why are all these people ringing our doorbell?” Just turns out that Old Saybrook still has neighbors that ring the doorbell every once in a while to say, “hey.”

I was working on my boat and had to set up a line to attach the anchor. I’ve never done this before, so I went on the town website and found the harbor master’s number. I’m thinking it’ll go straight to voicemail. Turns out it was his cell phone, he answered and came right over to help me out. Even had a bunch of tools and connections I needed. Actually, I just watched him do everything, but I learned so much! Thanks, Scott!

My husband had to leave extra early for work one day and of course didn’t leave me the car seat I needed to take the kids to school. I knew the family down the street had three kids similar in age to ours, so I walked over to their place and caught them having breakfast. I was so embarrassed, but they immediately put me at ease and let me use their car seat. They even offered to let me take their mini-van! The car seat was fine! Stop being so darn nice, Old Saybrook!

Our landscaper took us on out of pity because we were new to town and expecting kids. He had a full client list (like every other landscaper) but squeezed us in because he knew we had a lot going on. On top of mowing our lawn once a week, the gave us free snow removal and garbage pickup. Still haven’t gotten a bill, every time I text him he just sends me a thumbs up emoji. He’s the sweetest guy and he uses emojis! I finally went out and bought a mower because I didn’t want to take advantage of the situation and I think I offended him. My bad!

I ran into one of the town leaders while out and about and mentioned I thought some cars were driving a little too fast on my road. I really said it as more of a joke, the next day one of those speed trackers was out on our street. Coincidence? Maybe.

The local outdoors store is right in the middle of town off Main Street. I take my rambunctious three-year-old in there whenever we walk by, and he loves to play with the outdoor stuff, camping equipment, hammocks, and even zip himself into the tents to hide. I’m thinking, “These people are going to kick us out every time they see me walking up.” They just high five my kid and talk about how great kids are. I’ve never purchased anything from this store.

On our first night out in a while without the kids, we wrapped up dinner with a nightcap and dessert, and started talking with the owner of the restaurant. Turns out her husband is our electrician that saved the day for my neighbor after the storm. She didn’t charge us for dessert or drinks. Who are these people?!