The Greater Mystic Chamber of Commerce is pleased to shine a spotlight on Raylene Taskoski in our “Community Proud” series, sponsored by Charter Oak Credit Union.

Born and raised in southeastern Connecticut, Raylene has always considered the region home. Life has taken her to Alaska, Florida, and many destinations in between, but she has continued to find her way back to the shoreline, history, small businesses, and people that shaped her.

Raylene is the founder of Middle of the Vines, an all-inclusive vineyard tour company that combines several of the things she loves most: travel, local experiences, laughter, and meeting new people. “The best part isn’t even the wine,” Raylene said. “It’s watching complete strangers climb into the van in the morning and, five hours later, leave talking like they’ve known each other for years.”

Looking back, Raylene’s career has always centered on people. She spent 18 years in direct sales, earning 15 incentive trips throughout the country and around the world. She also became a motivational speaker and comedian, experiences that showed her how much can be accomplished when people are laughing, comfortable, and enjoying themselves.

Marketing eventually entered her professional life as a side business, but connecting with people remained the common thread throughout each stage of her career. Middle of the Vines now brings those experiences together. Raylene gets to meet interesting people, make them laugh, introduce them to local businesses, and send them home with stories they will remember long after the tour has ended.

The inspiration for the business came from Raylene and her husband, Mike’s, shared love of tours. Ghost tours, brewery tours, food tours, and excursions are often at the top of their travel itineraries. They enjoy having someone else manage the transportation, planning, and decisions while they experience a destination from a local perspective.

Raylene realized that southeastern Connecticut was filled with exceptional vineyards, but no one was offering the complete experience she wanted as a customer. She envisioned a tour that included transportation, a planned itinerary, lunch, and opportunities to meet new people. When she could not find it, she created it. Every detail of Middle of the Vines has been guided by one question: “Would I want to book this?” If the answer was no, Raylene knew it was not good enough.

Raylene wants every tour to have an impact beyond the vineyards. She hopes guests remember the coffee shop they visited before the tour, the boutique they discovered afterward, the restaurant someone recommended, and all the reasons they should return to Southeastern Connecticut.

That approach reflects her belief that a rising tide lifts all boats. Raylene has been encouraged by the willingness of local business owners to recommend, collaborate with, and support one another. She has seen vineyard owners promote neighboring vineyards, hotels recommend local restaurants, and business owners regularly ask how they can help. “That’s the kind of community I want to be part of,” she said.

For Raylene, trust is built by doing what you say you will do, showing up, and genuinely wanting others to succeed. Some of her favorite conversations with fellow business owners begin with the words, “I have an idea.” Those conversations often lead to partnerships that benefit everyone involved.

Chambers of Commerce have played an important role throughout Raylene’s entrepreneurial journey. She was a member of the Greater Norwich Area Chamber of Commerce during her earlier ventures and joined the Orlando Regional Chamber of Commerce while operating a business in Florida. Today, she is involved with both the Greater Mystic Chamber of Commerce and the Eastern Connecitcut Chamber of Commerce where she participated in the Entrepreneur Academy. She credits the Chambers for hosting great networking events and introducing her to supportive people and new partnership opportunities. 

Raylene has been proud to donate vineyard tours to local fundraisers and develop relationships with hotels, restaurants, vineyards, and attractions throughout the region. Each partnership gives her another opportunity to introduce people to the businesses and experiences that make southeastern Connecticut special.

Being recognized through the Community Proud series is especially meaningful to Raylene because she understands how uncertain starting a business can feel. “Starting a business is exciting and terrifying,” she said. “There are plenty of days when you’re wondering if you’re doing the right thing or if anyone even notices all the work happening behind the scenes.”

Learning that someone took the time to nominate her was incredibly humbling. Professionally, the recognition reassures Raylene that she is building the meaningful relationships she hoped to create. Personally, it reminds her why she started Middle of the Vines: to introduce others to a community she is proud to call home.

Raylene spent four years living in Alaska and another five years in Orlando. Although she treasures those experiences, they strengthened her appreciation for southeastern Connecticut.  “Sometimes you have to leave home to truly appreciate it,” she said.

For Raylene, home is where her roots are. Her parents and brothers are here, along with many of her favorite memories. While her three daughters and three grandsons now live elsewhere, southeastern Connecticut remains the place where Raylene learned the importance of community.

Today, she has the privilege of sharing the place she has loved throughout her life and watching visitors fall in love with it, too.

Her daughters remain one of her greatest sources of inspiration. Watching them build lives across the country and around the world has encouraged Raylene to continue saying yes to adventures and challenges. They have reminded her that growth often requires taking a chance, even when the next step feels uncertain.

Raylene has always possessed a “What if?” personality. What if someone offered vineyard tours in southeastern Connecticut? What if she could create an experience people continued talking about long after it ended? Those questions keep her curious and excited about what may come next.

Her willingness to take on ambitious challenges began long before Middle of the Vines. In her early 30s, Raylene ran a marathon and several half-marathons while also completing multiple triathlons. She trained with a group, which seems fitting for someone who has always been happiest when accomplishing something alongside other people.

Those races taught her about perseverance and the rewards that can come from attempting something that initially feels out of reach. They also revealed another source of motivation: proving wrong anyone who believed she could not do it.

Outside of work, Raylene enjoys gardening, cruising, exploring new destinations, trying local restaurants, and spending time with her family. Her garden has become her happy place, where she enjoys planting seeds and watching them grow, at least until the zucchini begins producing more than any household could reasonably need.

During the winter, Raylene can often be found completing a jigsaw puzzle in front of the pellet stove while planning her next cruise and wishing she were already aboard the ship. No matter the season, she is usually searching for her next excursion or opportunity to make a memory.

Middle of the Vines may have grown from Raylene’s idea, but she is quick to recognize the family members who helped make it possible. Her husband, Mike, believed in the vision from the beginning. Her daughters have consistently encouraged her, while her parents supported the business both emotionally and financially.

“Starting a business is never a solo journey,” Raylene said. “Middle of the Vines may have my name on it, but it’s been built with a whole lot of love, encouragement, and faith from the people who mean the most to me.”

Through Middle of the Vines, Raylene is doing far more than transporting guests between vineyards. She is creating friendships, promoting local businesses, and helping visitors discover the community she has always been proud to call home.