5 tips for Wining and Dining Yourself

Hi there! I am El Stevens and recently I have started solo adventuring to different places and events. As I approach 30, I have grown to realize that I actually have a ton of fun by myself! I have discovered that I am actually pretty funny and I have a terrible sense of direction although my husband says the latter discovery is old news. Anyways, I enjoy researching and checking out local spots around Connecticut – including many wineries.

I know what you’re thinking, “Does this lady have any friends?” I have to admit, I can probably be described as a crazy cat lady, but the honest answer to that question is: Yes! I actually I have a ton of friends. I am sure we can all think of a handful of scenarios when we have asked a friend to check out a new movie, catch a concert or visit a winery and unfortunately, they were busy. Then, maybe we called another friend only to find they were busy too. After a few tries we most likely felt a little defeated, threw on some sweats and plopped down on the couch for the rest of the night. Am I right? If this has never happened to you then you must be in denial or the coolest person ever.

My suggestion to you is go to the movie, catch the concert and go to the winery – GASP – alone! You may be pleasantly surprised how much fun you have by yourself. What do you have to lose? It has to be more exciting than the Keeping up with the Kardashians episode you have seen 10 times.

Here are some solo adventuring winery tips for you:

img_83491) Find the Right Winery

Picking the right winery for your solo adventuring personality is key! Whether you are looking for a bustling environment with a lot of people or more of a laid back and peaceful ambiance, do a little research to pick a good fit. Maybe pick a few wineries that are close together and this way you can hop around and find one that feels right. My favorite solo winery spot? White Silo Farm & Winery.

2) Give Yourself a Pep Talk

There will most likely be that moment when you shut off the car engine and you are about to step out of your car, alone. Give yourself a little pep talk, “You are a confident woman, you are wining and dining yourself today, your outfit is on point.” You are alone and fabulous – go for it!

3) Talk to People & Bring a Hobby 

Talk with people. Yes, strangers! An easy way to make this happen is to join a tasting group. Everyone will be listening to the tasting room attendant, asking questions and voicing which wines they enjoy. This is a perfect time to chime in and get some conversations going. If the question comes up, “Who are you here with?” be honest and say you are by yourself. Trust me, this gets the conversation flowing with many questions and people are typically impressed. You may even inspire them to do some solo-adventuring, too.

It is always a great idea to bring a hobby! Maybe you love reading or you would like to capture some awesome photos. If this is the case, bring your favorite book and/or your camera. You could skip the tasting all together, buy a glass of wine, sit and relax with a book. Or, walk around the winery and discover every nook and cranny through your lens. Both hobbies are a great crutch and can also lead to conversations.

img_83664) Be Smart
Alright, so you’re alone at a winery. Unless you took an Uber or your neighbor owns a winery then you are most likely driving yourself home which means you need to plan ahead and be smart. Maybe you only do half of the wine tasting or choose to have just one glass of wine. Make sure to hydrate ahead of time and bring water with you. Many of the wineries also allow you to bring snacks. Do your research and be smart! No one wants a solo adventure to jail.

5) Have Someone Take your Picture

Whether you have a professional camera with you or just your iphone, make sure to have someone snap your picture. All of the wineries on the CT Wine Trail are beyond beautiful and lets face it if you don’t Instagram it – did your solo adventuring wine day even happen?


Ellen Stevens

El is a wine enthusiast residing in New Haven, CT with her veggie-loving orange cat, Razz, and her football-coaching husband, Jordan. She is a lifestyle and documentary photographer and co-owns a creative company, E&H Creates, with her sister Hannah. Together, the dynamic duo makes the world a little more beautiful.


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