As it meanders along Esopus Creek and plunges into the Catskills Mountains, Highway 28 from Kingston to Phenicia offers an endless array of food and drink options, trailheads and shopping spots.

It has to be one of the most action-packed 20 miles of road in America (talking to you, Route 66), where you can get your kicks on a road that winds its way through West Hurley, Shokan, Boiceville and Mt. Tremper . There’s no way to visit all of the chosen spots in one day – well, that would be one heck of a day – but it’s a drive you’ll want to do more than once, given the stunning scenery. Or, better yet, check into one of the hotels along the route and have a great vacation.

Heading west from Kingston, start by buying comfortable walking shoes or a windbreaker from a family business Kenco Outfitter (1000 Hurley Mt Rd, just off NY-28), then seek an encounter with the Buddha at Tibetan Center (875 NY-28)which offers meditation classes, many cultural events and a gift shop.

Prepare yourself more for the road ahead with a popular breakfast sandwich at Mara is on her way (855 NY-28) and you will be well fueled for the first hiking stop at Lake Onteora Trail. Keep an eye out for the trailhead sign on the north side of the road – and remember key tips to stay prepared for tick season.

After a short hike to the slender and lovely lake, the next must stop is at West Hurley at the Woodstock Art Exchange (1396 NY-28) which features an array of local art, as well as glass sculptures by founder Pablo Weinschenk. Stack all the purchases in the car and head to the Ashokan Rail Trail – Woodstock Dyke (1285 NY-28), the next tempting path to explore. The path feeds into the larger 11.5-mile trail that runs along the Ashokan Reservoir.

Want to turn a day trip on Route 28 into a weekend getaway? The Dylan Hotel in Woodstock is one of three bonus hotel options on the list; the decoration and the equipment of the accommodation reflect the artistic and musical atmosphere of the region.

Daryl Jack

It’s a little early in the road trip to bail out, but know that the Hotel Dylan (320 Maverick Road, just off NY-28) provides shelter from the storm, or the Storm King so to speak. The hotel has a pool, fire pit, and reasonable rates if you want a base from which to tackle other places on this list or save them for another day. A quick stop at Abandoned hard cider tasting room at the hotel is refreshing even if you don’t book a night at the hotel.

Just up the east road Veneration (2440 NY-28)a vintage clothing boutique where “religion is creativity” that offers independent designer duds and vintage clothing and accessories for men and women, as well as all kinds of arty specialty items.

No Hudson Valley road trip is complete without some antiquing, and the diminutive Memories (3038 NY-28) tick this box – blink and you’ll miss it, so keep an eye out. Now expect to be teased out of your car via another trail to a heavenly view of the Catskill Mountains at the Ashokan Rail Trail – Ashokan Station (3045 NY-28).

Post-hike snack alert: Get your chocolate fix at Fruition Chocolate Works (3091 NY-28), where free trade chocolate bars feature flavors such as Bourbon Dark Milk. You probably won’t see any moose today, so visit moose crossing (1 Reservoir Road to NY-28) for rustic wooden furniture that will maintain the rustic vibe. They also offer a really cool selection of handmade knives.

Steve Heller's Fabulous Furniture makes state-of-the-art pieces like this spalted maple table.  The shop also features a garden of mini metal robot sculptures, vintage hot rods, and scrap metal parts.

Steve Heller’s Fabulous Furniture makes state-of-the-art pieces like this spalted maple table. The shop also features a garden of mini metal robot sculptures, vintage hot rods, and scrap metal parts.

Martha Frankel

It’s time for the next outdoor stop in the city of Olive’s Grant Avery Park (39 Bostock Road), a rolling multipurpose space that has a play area for children. Keep an eye out for the sign and walk up Bostock Road a few meters to access the park.


Get back in the car to visit Steve Heller fabulous furniture (3930 NY-28), which features stylish wooden furniture and funky furniture made from vintage cars and scrap metal. Bake alert: Are you near the Boiceville location of Bread Only Bakery (3962 NY-28), a family-owned organic bakery powered by solar energy and certified climate-neutral.

After a croissant and a coffee, the next stop is more artistic. the Brunel Sculpture Garden is an absolute gem in the Catskills, home to over a dozen statues and sculptures by French artist Emile Brunel. The establishment also welcomes artists in residence and organizes all kinds of events and conferences.

Back on the road and nearby is the third Ashokan Rail Trail route, this time to Starting point of the Boiceville bridge (5080 NY-28). Go out for a short walk.

The Emile Brunel Sculpture Studio and Garden, also known as Totem Indian Trading Post, Le Chalet Indien, and Brunel Park, is home to more than a dozen statues, sculptures, and totem poles.

The Emile Brunel Sculpture Studio and Garden, also known as Totem Indian Trading Post, Le Chalet Indien, and Brunel Park, is home to more than a dozen statues, sculptures, and totem poles.

Jonas Finkel

You are now entering the heart of the Catskills, so take a look at the Catskills Visitor Center (5096 NY-28)which includes the Upper Esopus Fire Tower, nature trails and more on 60 acres of forest, fields and wetlands.

Ready for your first visit to the Road Trip farm? Migliorelli Farms (5200 NY-28) has you covered whatever the season, whether it’s peaches, strawberries or apples. And if you can’t find the perfect pint of cherries, damn it, there’s another farm stand practically next door. Tremper Hill Farms (5224 NY-28).

Time to call it a day? the majestic Foxfire Mountain House (72 Andrew Lane)just off route 28, is a renovated hostel with mountain views and a great bar.

You’ll want to devote time to the empire of interesting things at Emerson Resort and Spa (5340 NY-28) which contains a stack of retail stores – and the world’s largest kaleidoscope. It is also the home of the rustic and the stream Grid of wood notes (known to locals as Catamount) (5368 NY-28). Enjoy a drink and a view.

If you like budget foodtrucks, hot dog captain (5401 NY-28) delivers roadside sausage action. Quench the thirst with a pint of Mean Charlene Sour Ale nearby Woodstock Brewery (5581 NY-28).

Woodstock Brewing bartender Evan Odato pours a Woodstock Pilsner.

Woodstock Brewing bartender Evan Odato pours a Woodstock Pilsner.

Sarah Wolpoff

There is excellent trout fishing in these areas, and Esopus Creel Fly Fishing (5579 NY-28) has everything you need to try to catch your dinner – and if you don’t, old school Phenicia dinner (5681 NY-28) awaits your hungry soul (singer Lorde loves their onion rings).

the Railroad Explorers: Catskills Division (70 High Street at NY-28) will take you on an eight-mile electric pedal train that’s so much fun you’ll probably want to spend the night at the Phenicia Lodge (5987 NY-28) and hop on this train again in the morning – before hitting the departure points, shops and markets you couldn’t get to the day before.

As you return to your starting point, enjoy a meal at the welcoming and spartan Hickory barbecue and smoker (743 NY-28) in Kingston and call it a day – or two of them.

Now up thatRoad 66!

More trips to the Hudson Valley