The ultimate 3-day guide to Dutchess County in New York State

Thrilling rides on vintage planes, a culinary institute that started the careers of many famous chefs and natural beauty abounds: why New York State’s Dutchess County is the perfect getaway.

Some place names are known to us all as the long weekend holiday haven for New Yorkers: the Hamptons, Maine, Rhode Island. Upstate New York will be on many lips, but you may not have heard of Rhinebeck and the wider Dutchess County, but you should put it firmly on your travel list.

You could easily stay in Dutchess County for a week, but being under two hours from New York City, it’s the perfect way to relax after the hustle and bustle of the Big Apple. It’s a secret that many city dwellers and celebrities have discovered (Paul Rudd even co-owns a candy store here), but not so many tourists.

Drive through the natural beauty and quaint towns of Dutchess County. (Image: Ricardo Costa)

This is also a county that is incredibly fond of a festival – from arts and crafts to jazz to county fairs – but even if you can’t time your trip to coincide, this three-day itinerary will give you plenty of reasons to make the train ride down to Dutchess County.

Day 1

8am: Head to Moynihan Train Hall in New York and take a scenic train ride along the majestic Hudson River until you get to Rhinecliff Train Station. The just-under-two-hour trip will fly by as you enjoy the scenery out your window.

10am: Stretch your legs at Minnewaska State Park Preserve. Part of the Shawangunk Mountain Ridge, Minnewaska’s rugged and rocky terrain gives visitors plenty of ways to explore. Head off on foot, bike or horse, explore below the park’s three lakes by scuba diving (or hire a boat and stay on the surface) and get a bird’s-eye view with some of the best rock-climbing in the world at The Gunks.

Keep an eye out for the wildlife at Minnewaska State Park Preserve. (Image: Tom Dils)

1pm: Drive to Beacon, considered the art hub of Dutchess County, bringing creatives from all over the country. The mecca of this artsy mecca is the completely unique Dia Beacon gallery. Have lunch at the attached cafe, then take your time wandering through this large, former industrial building on the banks of the Hudson River. Housing large-scale art by world-renowned artists, the installation of the works is almost art in itself. The gallery relies entirely on natural light, and therefore only opens during daylight hours: a fact that many artists use to their advantage when deciding how to use the space.

Discover why Dia Beacon is unlike any other art gallery. (Image: Kassia Byrnes)

2.30pm: Spend the afternoon wandering the streets of Beacon. See the beautiful designs in Hudson Beach Glass (and maybe even make your own during a glass-blowing class), discover local talent at the free art exhibits in BAU: Beacon Artist Union, taste locally crafted spirits at Denning’s Point Distillery or treat yourself to dessert and live music at Towne Crier Cafe. Relax in Scenic Hudson’s Long Dock Park before jumping back in your car to explore spooky local ruins like Bannerman Castle and The Craig House Institute.

Taste locally crafted spirits at Denning’s Point Distillery.

4.30pm: Because it’s impossible to get sick of Hudson River views, catch the elevator to the top of the world’s longest elevated pedestrian bridge: Walkway Over the Hudson. Time your walk right as the sun starts to set. Whether you complete the whole walk or turn around somewhere in the middle, from here you can see sweeping 360-degree views of the Catskills mountains.

Walk across the world’s longest elevated pedestrian bridge. (Image: Mark Steinmetz)

6pm: Check into the bright, eclectic and intimate Hotel Tivoli in the historic town of the same name. This university town has a funky edge all its own, which has been enhanced and polished by hotel owners and painters by trade, Brice and Helen Marden. Their sharp eye has filled the 11 guest rooms inside this century-old building with an eye-catching collection of furniture, lighting and art. Luckily, onsite farm-to-table restaurant The Corner is also the perfect place for dinner, showcasing local produce and Mediterranean flavours. And let’s not forget the curated list of local and international wines.

Head down to The Corner for dinner. (Image: Emma Tuccillo)

Day 2

9am: Enjoy a lazy breakfast at one of many popular cafes near your hotel. Try Tivoli Bread & Baking for a meal, while All That Java is the best spot for a coffee-to-go.

11am: Whether you’re a fan of aviation or not, Old Rhinebeck Aerodrome presents an absolute bucket list experience you never knew should be at the top of your list. While the onsite museum and hangers filled with some of the oldest planes in aviation history are very interesting, it’s the rides in a bi-plane that really make this experience. Open for joy flights around June, take to the sky in a 1929 New Standard plane replica (complete with original engine). Your pilot is also one of the plane’s engineers, which is a comforting thought as they perform wingovers and humptys high above Rhinebeck and the wider Dutchess County. With the wind whipping around your head (protected by a cap and goggles, of course), this is the most exhilarating rollercoaster you’ll ever go on. Flights are around $150, plus tip.

Get the thrill of wingovers and humptys in a 1929 New Standard biplane replica.

1pm: Take a trip into Dutchess County’s ritzy past with a tour through the Staatsburgh State Historic Site. This 79-room mansion was once the home of Ruth Livingston and Ogden Mills, and today is a relic of the glamourous Gilded Age. After you’ve seen the house, explore the grounds – edged by the Hudson River – via hiking trails.

Take a step back in time at Staatsburgh State Historic Site. (Image: Kassia Byrnes)

2pm: Market Street, the main street of Rhinebeck, might be quaint, but it packs a punch when it comes to cafes, restaurants and shops. Perhaps it’s the organic chickpeas, but Aba’s Falafel has the best falafel you’ll ever taste. Village Pizza continues to be voted the best pizza in Hudson Valley, The Amsterdam serves up classic American meals and inviting decor, while Willow at Mirbeau infuses French flavours with the best produce from local farms, food artisans, and craft distillers.

Enjoy the best falafel of your life at Aba’s Falafel. (Image: Kassia)

After lunch, wander the nearby shops, offering everything from hand-crafted fashion to locally made crafts, to a famous-by-association candy store. Samuel’s Sweet Shop is owned by Paul Rudd (yes THE Paul Rudd), his wife Julie and fellow actors Hilarie Burton and Jeffrey Dean Morgan and Andy Ostroy. How did such a famous crowd come to own a small-town lolly store? As long-time fans of Rhinebeck, they knew the original owner Ira Gutner. When he passed away, the celebrities banded together to save the store from going under – which is almost as sweet as their wares.

Stop by Paul Rudd’s candy store in Rhinebeck. (Image: Kassia Byrnes)

5pm: Pop over to Bard College where you will find one of the sweetest riverfront, walled gardens in the state. Beginning life in 1835, the 38-hectare estate on which Blithewood Garden sits was designed by one of the best landscape gardeners of the day, Andrew Jackson Downing. Now, it’s an incredibly peaceful place to sit and enjoy the blooming flowers. Grab a quick bite From nearby Red Hook to bring with you and sit in the neighbouring fields to enjoy a picnic as the sun goes down.

Stroll Blithewood Garden. (Image: Kassia Byrnes)

7.30pm: Walk over to the on-campus performing arts centre, The Fisher Center, to catch a show. Here you will sit down to no standard university performance. With a rolling calendar of diverse performances, the likes of Peter Dinklage have graced this stage, while Steely Dan and Chevvy Chase studied at this premier performing arts college. The building itself, designed by world-renowned architect Frank Gehry, is reason alone to visit. Or time your visit for the annual Summerscape Festival; eight weeks of opera, theatre, music, cabaret, film and dance held from June to August.

10pm: Head back to your hotel for a satisfying slumber.

Catch a show at the architecturally significant Fisher Centre.

Day 3

9am: Stop into the Aussie-owned and run Tivoli General for a coffee to kickstart the day, and freshly made sandwiches that will become your picnic lunch.

10am: Why a picnic lunch? Because you’re heading to one of the world’s 10 best gardens, Innisfree Garden. Designed by landscape architect Lester Collins, these approximately 80-hectare gardens took 50 years to perfect, and the result is magical. More like a highly curated national park than a traditional garden, merging the modernist and the romantic with traditional Chinese and Japanese garden design principles. The result is a dreamy, zen landscape begging you to slow down and take your time. Each year, events are scheduled here so you could always check the calendar and time your visit accordingly – just note that the garden is closed in the colder months.

Picnic in one of the world’s 10 best gardens. (Image: Kassia Byrnes)

1pm: If you’ve ever wondered where some of the world’s best chefs – like Anthony Bourdain and Julia Child – first honed their craft, that answer is The Culinary Institute of America (CIA)., CIA has been doling out an education in the professional culinary field since opening in 1946 (and moving to its current campus in 1970). You might not have time to enrol, but you do have time to stop by one of five permanent onsite restaurants and eateries where these students put their notes into practice. Run as fine-dining (though keep in mind these are trainees, so be patient), you’ll find amiable service and mouth-watering dishes. Sit down to French, Italian or classic American, or find more casual fare in Apple Pie Bakery Café or The Brewery. There are also several wine-tasting workshops you can sign up for. Whatever you choose, it’s a delicious way to end your trip.

Treat yourself to Italian at Ristorante Caterina de’ Medici.

Getting around and other tips

You might not need a car in New York, but you will need to hire one here. The roads are quiet and easy to navigate, and you don’t want to be relying on public transport.

To enjoy the peace and quiet of local life, not to mention lower rates (it’s actually cheaper to stay in Manhatten on a weekend rather than stay in Dutchess County), try to avoid the weekends.