Our Stay in Stamford, NY

New York

October 2025

Fall on the Hills of Stamford, New York

After a two-day visit, we left Erie and Pennsylvania behind and drove 350 miles to settle into a cozy Airbnb early in the afternoon. Once everything was Hemmes-ready, I couldn’t resist grabbing my camera to take a few photos of this charming spot tucked into the colorful hills of Stamford, the “Queen of the Catskills.” We instantly knew we would love every minute of our seven-day stay here.

A Runner’s Reality Check in the Catskills

This week also marked the start of my Ten-Miler Program, under the virtual guidance of my Dutch coach. Here in the Catskill Mountains, with their steep ups and downs, I was therefore glad to find a converted rail trail to run on! My sights are set high — just a few weeks ago, I finished a 10K (6.2 miles), and now I’m training for a 10-miler (16.2 km).

Whether I’ll actually be ready by December is still up in the air, since today didn’t go quite as I’d hoped. After reaching my turnaround point, I hit the proverbial wall. I tried to keep jogging at a slower pace, but eventually ended up walking back to the car. Yesterday’s mountain hike and today’s sneaky false flat caught up with me. Even for active “young at hearts” like me, staying “young at heart” sometimes means admitting that recovery takes a little more time.

A Stroll Downtown Stamford, NY

In the afternoon, we drove to downtown Stamford, NY, and parked on Main Street. The town has such a rich past. It was once a popular mountain resort where wealthy visitors from New York City came for fresh air, grand hotels, and stunning mountain views. We saw traces of that history in the town’s historic buildings.

By the mid-20th century, the trains stopped bringing passengers. Today, resilient Stamford honors its tourist heritage, drawing visitors who embrace the Catskills’ beautiful mountains with activities for every season. In addition to the excellent hiking trails, we were, ofcourse, also treated to the gorgeous colors of the season.

When Nature Calls, A Run Interrupted!

Two days later, I hit the trail for another long, slow run on a crisp, sunny day. I went in the opposite direction this time, starting with the slow ascent. About 50 minutes in, just as I returned to the car, I called it quits, not from tired legs, but simply because Mother Nature called.

One Last Run Before Goodbye

On our last day in town, we began the morning with a run, once again starting near the old train station. Since it had rained all night, the trails were still a bit wet, and I had to zigzag around a few puddles; however, overall, it was totally doable. I finished my planned distance, feeling good, and decided to walk a bit to cool down while waiting for my husband. I headed in his direction and soon spotted him running toward me — my cue to turn back and head to the car.

Churchill Park Historic District, A Gilded Age Gem

After a quick shower and lunch, we tried to squeeze in a few more must-dos around the Stamford area — places we hadn’t had time to visit before. We returned to Stamford Downtown to explore the Churchill Park Historic District, which has been part of the National Register of Historic Places since 1980.

The district is named after Dr. Stephen E. Churchill, who helped bring prosperity to the village by supporting projects like the local water and sewage systems, the construction of hotels, and the establishment of the Stamford Village Library. The area’s charming nickname, “The Queen of the Catskills,” is often linked to him.

The neighborhood around Churchill Park felt like a step back in time. The graceful Victorian homes, with their verandas and decorated woodwork, reflected Stamford’s Gilded Age as a summer resort town. It’s easy to see why this small mountain village once drew wealthy visitors from New York City.

Checking Out Again, Our Catskills Goodbye

And a week later, it was time to say goodbye to our home away from home in Stamford, NY. The cozy, stylish, and spotless cottage, set on a peaceful hilltop with colorful trees and stunning mountain views, had been the perfect base for our first trip to the Catskills.

We drove off early for a six-hour drive to Charleston, Vermont, ready for new adventures. Along the way, our car hit 100,000 miles — a fun milestone celebrating all the trips we’ve shared since we began our adventure traveling across the states in August 2020.