Catskills road trip: Fly fishing in charming Livingston Manor

Livingston Manor in the Catskills blends small-town charm with a deep connection to the outdoors.  A roughly three-hour drive from Long Island (two hours from New York City), it’s a place where you can spend the morning browsing quirky boutiques, the afternoon learning the art of fly fishing and the evening kicking back at a local brewery or hotel.

Here’s how to spend a perfect fall day (or two) in this Catskills gem:

Strolling Main Street

The heart of Livingston Manor is its compact, walkable main strip, where locally owned shops line the road in brightly painted storefronts.

Step into Seasons (8 Pearl St., seasonscatskills.com, 845-439-1155), a boutique that captures the town’s artsy spirit, with shelves full of carefully chosen home goods, ceramics and handmade gifts.

Formerly Concerte + Water in Williamsburg, Brooklyn, Seasons reopened in Livingston Manor in 2021. Owner Hannah Gluckstern says the new name was inspired by "the pieces you can have throughout your life no matter what season you’re in."

A block away, Jitterbug Sights & Sounds (67 Main St., jitterbugcatskills.com, 845-439-1447) offers a playful mix of records, vintage toys, art supplies and collectibles that feels equal parts nostalgia trip and treasure hunt.

Co-owners Miriam Rayevsky and Brad Mann describe it as "all things fun," noting that aside from turntables, nothing electronic interrupts the tactile experience of browsing.

Rayevsky says fall is the perfect time to visit. "It’s wildly busy in the summer. It’s definitely our most popular time. That makes it hard for folks to meet people or get the attention they want. It’s nice this time of year. You can find parking, you can talk to people, and you don't feel overwhelmed."

Every store has a personal touch, and that is part of the charm. Unlike larger Catskills destinations, Livingston Manor’s retail scene feels rooted in the community, where owners are often behind the counter ready to share stories and recommendations.

Fly Fishing capital

After a morning of shopping, it is time to see why anglers from around the world flock to this Sullivan County hamlet.  The town sits at the edge of Willowemoc Creek, one of the most storied trout streams in America. For more than a century, the Catskills have been considered the birthplace of American fly fishing, and the town remains a hub for those seeking a hands-on experience.

I met up with Jared Makowski, a guide at Dette Flies (13 Main St., detteflies.com, 845-439-1166), the oldest family-run fly shop in the country, founded in 1928. Letters from former President Jimmy Carter line the walls, thanking the shop for providing fly fishing gear, which is plentiful. A lesson costs $95 and includes waders, a rod and flies. You will need to purchase a $5 fishing license online at dec.ny.gov or by phone (1-866-933-2257) before heading out.

Learning the basics

At Dette Flies, Makowski helps first-timers learn the basics of a sport that looks deceptively simple, but requires patience, finesse and observation.

"The game here is fooling the fish into thinking that it’s a living insect floating down the stream that they’re going to eat," Makowski explained. "If we can’t properly cast to get the fly into position and get it to do that, then we’re at a disadvantage."

In other words, the fish will know we are faking it. "Absolutely," he laughed when I asked.

Lessons start on dry land. First comes the grip, a simple but essential detail, and then casting, which is all about rhythm. I started off whipping the line too quickly, but the more I practiced and watched him, the more I got the hang of it.

Fly fishing is a really fun way to fish because it’s very visual. You’re watching the line, the water, the insects, you’re part of the whole system.

— Jared Makowski, guide at Dette Flies fly shop in Livingston Manor

"Fly fishing is a really fun way to fish because it’s very visual," Makowski said. "You’re watching the line, the water, the insects, you’re part of the whole system."

Stepping into the water

Once I had the basics down, it was time to wade in. I strapped on waders for the first time and followed Makowski to Willowemoc Creek, settling on a beautiful spot underneath the Livingston Manor covered bridge.

The stream was low when I visited, due to a stretch of dry weather. That made fishing trickier, but Makowski pointed out what makes this creek special.

"We have clean water; we have cold water most of the year coming in from a lot of tributaries," he said. "And we have really good bug life, so it is great for fly fishing."

He showed me how tiny microcurrents make even a simple tuft of fur tied to a hook look like a living insect underwater. Lifting rocks, he pointed out clusters of nymphs clinging to the surface. This abundance of mayflies, stoneflies and caddisflies keeps trout well fed and anglers coming back.

Even without spotting any trout, the lesson was eye-opening. The fish conserve energy by resting in easy spots.

"They’ll push out of the current," Makowski explained. "They won’t be in the biggest parts where they have to fight and expend energy. These bugs get funneled down along the bank, and it is easy for a fish to just sit there and eat."

Suddenly the river felt less random and more like a carefully designed buffet line, with trout quietly staking out their favorite spots.

In the end, I didn’t catch any fish, but that wasn’t the point. The joy of fly fishing is about slowing down, noticing the details and connecting with nature in a way that’s equal parts meditative and playful.

Where to eat and stay

The Kaatskeller (39 Main St., thekaatskeller.com, 845-439-4339) offers wood-fired pizzas in a casual outdoor space with cornhole and bocce in the heart of town. Try the Wild One: pepperoni, smoked mozzarella, onion, harissa-spiked San Marzano tomato and pepper-infused honey ($28). Indoor dining and a cozy upstairs lounge complete the experience.

Just up the road, Upward Brewing Company (171 Main St., upwardkitchen.com, 845-439-1382) serves house-made beers in a warm inviting space and outdoor garden. The Black Grass pils-noir (6% alcohol by volume) is a standout, paired nicely with bratwurst ($14) or lemongrass chicken dumplings ($13).

For overnight stays, Callicoon Hills (1 Hills Resort Rd., callicoonhills.com, 845-482-2420) is a laid-back, century-old resort just 15 minutes from town. Choose an A-frame cabin starting at $129 a night, a queen ($152) or king ($189) room in the Boarding House. Don’t miss nightly s’mores around the fire at 5 p.m.

Livingston Manor makes it easy to enjoy both the outdoors and a charming small-town atmosphere. Between boutique shopping, riverside wading and local dining, the town is a perfect Catskills getaway not too far from Long Island.