Little Adventures, Big Difference: A Weekend in Guilford, Connecticut

Have you heard of Guilford, Connecticut? This small town was a spontaneous detour for Jeff and me that quickly became a highlight of our travels. We arrived with zero plans and left with a heart full of new memories—a beautiful reminder that sometimes the best experiences are the ones you never saw coming.

Where We Stayed

We found an absolute gem of an Airbnb hosted by the loveliest couple. Even though they lived on-site, the separate entrance gave us total privacy, while still allowing us access to their incredible outdoor space - a full setup with a pool, grill, and hot tub. While we weren't quite brave enough for the pool in that crisp air, we definitely made use of the hot tub!

The true 'above and beyond' moment, though? Knowing we were car-less New Yorkers, our hosts actually offered to be our personal chauffeurs whenever we needed a lift! Their hospitality turned a simple weekend stay into an unforgettable experience.

What We Did

The "Concrete Jungle" Detox: Nature & Orchards

Living in the "concrete jungle" (as Beyonce would say) meant that whenever we traveled, we made it a priority to find some true greenery. We found exactly that at the GLCT Kampmeyer Nature Preserve. It was a simple, well-marked path—honestly more of a refreshing stroll than a strenuous hike—but it was exactly the breath of fresh air we needed.

The next day, we headed to Bishop’s Orchard, a charming hybrid of a farmer’s market, winery, and orchard. After sipping on some crisp, homemade apple cider pressed right on-site, we wandered through rows of pumpkins. Before heading back out, we stopped inside to taste their fruit wine, which was incredibly light and refreshing.

A Raspberry Revelation

As we continued exploring the land, we stumbled upon an adventure neither of us had ever experienced: raspberry picking! I honestly didn't even know raspberries grew on vines, so it was as much a learning experience as it was a treat. We filled our buckets, saving them for a perfect late-night snack back at our Airbnb.

Dinner Under the Stars

By then, we were hungry for something more substantial than berries. Jeff had done some scouting and found The Place Restaurant, and it was such a unique find. The entire restaurant is outdoors—kitchen included! You can actually watch the chefs at work, giving the whole place a lively, backyard BBQ atmosphere. Their specialty is the grilled lobster, and let me tell you, it lived up to the hype. We were literally licking our fingers afterward!

Small Town, Big Impact

After a relaxing final evening, we had a quick breakfast the next morning before catching our ride back to the city to gear up for the work week. Even though it was a fast trip, we made every second count.

Big cities are unmatched for their energy, but there is something about a small-town escape that helps you re-center. It reminded us to appreciate the "little adventures"—sometimes those are the ones that make the biggest difference.