Back to the Mountain that Started it All: Talcott + New Gear + A Few Hawks Who Had Ideas

There's a version of this story that starts at the trailhead. But the real story starts at LL Bean.

We'd been sitting on a small collection of gift cards for a while, and when a great sale lined up perfectly, we decided it was time for a proper gear refresh before Hike #2. I will not pretend I am above the thrill of new gear. I got a great new jacket. Sam got boots and a hat he has already declared his favorite possession. And we picked up a few other items that have immediately earned their place in the pack — including an incredibly convenient water bottle and phone carrier that I'm already wondering how I hiked without.

As a family, we have fully leaned into our New England identity, which apparently comes with LL Bean membership as a rite of passage. I wasn't born here, but I have enthusiastically adopted the unofficial brand of our region. And standing there watching Sam browse the travel books near the register, I had one of those quiet little moments. He stopped at a shelf and got a faraway look in his eyes, imagining The Family Stride's story on those shelves one day. I don't know if it will happen, but I know that's exactly the kind of dream worth chasing.

Envisioning The Family Stride’s story here one day.

The Mountain

Talcott Mountain holds a special place in our family's story. It was the first hike Steve and I ever did together, about sixteen years ago.

We've brought Sam before too, though it's been a while. Two trips stand out in my memory. The first was a Mother's Day hike with the three of us plus my mom, when we watched a hang glider launch from the top. I still remember the collective gasp from the crowd as he stepped off the edge, and then the long exhale of relief as the wind caught him and he swept up and away. The second trip was less cinematic. Sam was much younger, and after touring the Heublein Tower, he liked it so much that he absolutely refused to leave. He screamed and cried the entire way down the mountain. What made it slightly more memorable was that we passed some of my company's senior executives on the descent — and if you've ever wished the earth would simply open up and swallow you whole, you understand exactly how I felt in that moment. They probably recognized me anyway.

The Drive Up

The route to Talcott Mountain is genuinely one of my favorite little pockets of Connecticut. On the way, we passed through the historic East Weatogue district, admiring the beautiful colonial homes, and drove by Rosedale Farms and Vineyards. Operating since 1920, the farm has a wonderful origin story — it began when Morris and Minnie Epstein immigrated from Eastern Europe and took a leap of faith on a 40-acre dairy and tobacco farm. When Morris passed away tragically in 1927, their teenage son Louis stepped up to keep it going, and three generations later it's still a thriving family operation. Their farm stand is one of the best around. They host occasional live music and extraordinary Chef-to-Farm dinners with Max Hospitality throughout the season; in fall, there's a sunflower stroll and corn maze. It's one of those local gems that makes our corner of the world feel quietly special.

If you're ever heading up to Talcott in the fall, keep your eyes open for the house right before the park entrance — they do the most elaborately wonderful Halloween displays. You'll know it by the Super Mario mailbox.

The Hike

Talcott Mountain is not a difficult hike overall. But the first section is a steep climb, and it does not ease you in gently. By the time we reached the point where the trail levels off onto the ridge, I was huffing and puffing and had needed several stops on the way up. I'm not going to sugarcoat it — I was winded in a way that was a little humbling.

But that's also sort of the point of doing this, isn't it? I hope that by the end of the year I'm looking back at that climb with some perspective on how much has changed since then.

Once you crest the ridge, though, the whole world opens up.

The Farmington Valley stretches out in every direction and the view is genuinely stunning. Sam immediately spotted the Pinchot Sycamore and pointed it out to Steve with great confidence — it's the largest tree in Connecticut, a massive sycamore that has stood in the Farmington Valley for centuries. We walked along the ridge for a stretch, stopping to take it all in.

The Tower

The Heublein Tower is an iconic landmark with a genuinely great origin story. Gilbert Heublein was hiking on Talcott Mountain with his fiancée Louise when he promised her he would one day build her a castle there. He followed through: the 165-foot tower was completed in 1914 and served as their summer home and retreat. The six-story structure included luxurious bedrooms, living spaces, a ballroom, and the state's first residential elevator. It's been on the National Register of Historic Places since 1983, and the list of famous guests over the years is remarkable — it's where the Republican Party asked General Eisenhower to run for president, and Ronald Reagan visited in the 1950s while he was president of the Screen Actors Guild.

Which brings us to the barbecue pit.

Steve (our family's self-appointed grill master) took one look at that pit and immediately began mentally planning everything he could cook on a grill that size. The man has vision.

The tower was closed during our visit, but that's actually fine by us. We have a reason to go back when it's open, and when we do, we'll capture the observation deck and its famously sweeping views — on a clear day you can see Mount Monadnock in New Hampshire, the Berkshires to the northwest, and a thin blue streak of Long Island Sound to the south. That chapter is coming.

The spot where Simsbury, Bloomfield, and Avon meet.

We snacked in the pavilion with the valley spread out in front of us. This is the same pavilion where Steve and I have eaten our Hike to the Mic bagels on more than one Sunday morning — the festival is a late summer weekend tradition, with music all weekend and usually a jazz musician on Sunday mornings. There is something deeply satisfying about returning to a place with different layers of memory attached to it.

The Hawks (and a Man and His Dog)

On our way back down, we met a man we'd been leapfrogging past throughout the hike — passing each other, stopping, trading the favor of taking pictures for one another. He mentioned it had been years since he'd been to Talcott, that he used to come regularly with his golden retriever. His dog had since passed, and he was carrying his ashes with him on the hike.

It was one of those quiet trail moments that stays with you. It made us think — there are so many interesting people you meet on trails, each with their own reasons for being there. We've started talking about a future chapter of The Family Stride dedicated just to the people we encounter along the way.

And then, just before we headed back to the car, a group of hawks started circling overhead. Lazy, slow circles. Very much in the way of something that has spotted a potential lunch.

"They must be looking for some food to grab," I said.

"Hopefully they don't pick us," Sam replied.

I told him we were probably too heavy. But if our dog Charlie had been with us, I'd have been genuinely concerned.

The Walk Back Down

We spent most of the descent planning future hikes. The list grew fast — new trails, returns to old favorites, destinations scattered across New England. Talcott is part of the larger Metacomet Trail that runs through Connecticut, and we've started thinking about whether we could use sections of it for training as we build toward our bigger goals. There's even a version of this where we turn it into an inn-to-inn hike if we can convince our family to schlep our gear between stops. No promises on that one.

Hike #2 is in the books. Sam asked this week when we're planning the next one. Honestly, that question is the whole reason we're doing this.

Want to follow along as we train toward our big English long-distance trail goals? Subscribe to the blog, find us on Instagram and Facebook @thefamilystride, and check out our YouTube channel for the full hike video.

Back to the Mountain that Started it All: Talcott + New Gear + A Few Hawks Who Had Ideas

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