Jennifer Gallagher of Cobblestones in Beacon Hill

Jennifer Gallagher: Cobblestones of Beacon Hill Was Destined to Be!

Jennifer Gallagher is an ethusiastic, hard-working mom of three whose drive and determination have led her down the yellow brick (or should we say cobblestoned :-) road to owning and operating Cobblestones, a vibrant eatery on Beacon Hill, Boston.

I first discovered Jen when she spoke at the Beacon Hill Women’s Forum, where she was introduced as a female local business owner.

At the podium, she shared the story of discovering Charles Street and the auspicious path she followed to becoming the owner. What she shared with the group was remarkable! I glanced around and saw all the women around me mesmerized.

I wanted to retell her story here, so I reached out. And thankfully, she agreed to meet!

Here’s what Jennifer Gallagher of Cobblestones had to say:

RCG: Hi Jen! Thanks so much for agreeing to talk.

You’ve had such an exciting journey here to Cobblestones! Do you have any advice to share with women who have big dreams but don’t know how to begin?

Jen: Sure! Thanks for stopping by.

I have to start with my father. He was a very accomplished army general, and he taught me particular things. His words of wisdom include, “The harder you work, the luckier you get,” and, “You have to go with your instincts.

When you know, and you pray on it, through instincts, you know what’s best. And when you know what you’re capable of, that opportunity may become a reality!”

Another thing I can add is that when those opportunities arise, don’t ignore them. Take advantage, and work to develop them.

In this case, I did a lot of market research and had to choose whether or not this was a viable opportunity. After doing that, I decided to go for it.

More on how she was able to acquire the business:

RCG: That’s such a good point. You have to do your part, too. You need the courage to move forward, investigate, and discover people who can help you.

Jen: Yes, you must have the energy, determination, drive, and tenacity to make it happen. And to understand that ‘no’ is not an option.

Of note, I believe there are no coincidences in this world.

In fact, I have a great story to share.

The day I signed the purchase of sale, I remember walking up the stairs in my home and my eyes landed on one picture. It was a photograph of this exact building I’ve owned for the past 25 years.

Seeing that made me realize there’s a reason for all of this! It just felt right.

Back then. I couldn’t have imagined all the joy this business would bring me.

local art work from Cobblestones on Beacon Hill

Local artwork hung along big, bright windows at Cobblestones

What she likes most about owning Cobblestones:

RCG: What’s something you love the most about this business?

Jen: The people and the dogs. The locals, this community.

I love hearing people say, “Let’s bike to Cobblestones!” Or. “Let’s go see Jen at Cobblestones!”

It’s so exciting for me to realize we’re a destination!

Playing a role in lifting someone’s day and providing healthy food. These things make me feel grateful for what I get to do.

RCG: So good!

Jen: Another is having people walk in after seeing this location run down for many years say, “Wow! How’d you get here? This looks great!” I always say, “One step at a time.”

RCG: Very cool. I have to say, I love the artwork, too! And it adds a lot to the feel of a community space.

Jen: Yes, exactly! And in the new year, we’ll start working with the Berklee School of Music. We’ll have small groups of performers come in and play for the community to enjoy.

RCG: I love that. How did you decide on that?

Jen: I think music flows from art. It feels like a natural progression from art to music.

RCG: Agree. I’m looking forward to visiting during one of those performances. So, one final question: Where do you go to feel connected and surrounded by beauty?

Jen: There are two places. One is the woods and mountains. I love running with my dogs through the woods. Number two is the beach. We have a family home on a beach private beach. And there’s nothing like it. Nature is where I feel connected.

RCG: Wow! Very Thank you so much for taking the time to share this story. I’m very grateful.

Jen: My pleasure. Thank you for having me!


More on Jennifer Gallagher of Cobblestones:

Didn’t you find Jennifer Gallagher’s journey to Cobblestones very inspiring? If so, please share with someone who has got a new idea percolating. This story might be what they need right now!

You can visit Cobblestones at 30 Charles Street on Beacon Hill in Boston, MA.

And you can follow her journey on Instagram here.


To read another woman’s story of owning her own business, check out Ionica Brito’s here.

And, to read about another woman’s journey to Umbria, check this out!

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