13 Old School Things to Do in Rhinebeck NY: Hudson Valley Getaway for 250 Years

WHY GO: As with the Adirondacks – a few hours north, there are several things to do in Rhinebeck NY that your grandparents might have done.

Perhaps they stayed at the Beekman Arms Hotel (opened in 1766), dined at Foster’s Coach House Tavern (opened 1890), shopped on Market Street in town, or took in an airshow at the Rhinebeck Aerodrome (opened in 1956). Or maybe they took a Sunday Drive to ogle the fine mansions along the Hudson River.

Yes, the Hudson River’s Millionaire’s Row or “Great Estates” region is indeed beautiful to behold. Perhaps that’s why our moneyed ancestors (some of ours, anyway) chose to position their homes on the banks of this majestic waterway. The village of Rhinebeck NY, in Dutchess County New York, has been welcoming guests for over 250 years.

Experience the country’s first Barnstorming Aerodrome, adorable shops and sophisticated cuisine. Go romantically old-school on this Rhinebeck NY getaway. And, while you’re in the mood, check out these many other Romantic Getaways in New York State.

Where Is Rhinebeck New York?

Rhinebeck is located 100 miles (2 hours) north of New York City in New York State’s Hudson River Valley.

Best Things to Do In Rhinebeck NY And Red Hook

Old Rhinebeck Aerodrome

GO: Old Rhinebeck Aerodrome, Red Hook

The first of its kind in the USA, The Old Rhinebeck Aerodrome recaptures the thrill of bi-and-tri-plane flying, featuring WW1 and Barnstorming aircraft. Over a dozen planes – out of 60 in the collection – are “air worthy,” and star in some pretty daredevil stunts.

Airport field at Rhinebeck Aerodrome

In 1958, aviation mechanic, pilot, and Aerodrome founder, Cole Palen, purchased this Rhinebeck farm dirt cheap, as the home was site of an unsolved murder.

He started flying his collection of WWI planes for friends, and word spread of his derring do.

Red Barron Fokker, Tri-Plane

Years ago, the replica of Snoopy’s Sopwith Camel vied with “World War I Flying Ace, the Red Baron” as the hit song played. With Palen flair, the show morphed into a melodrama featuring the daring Sir Percy Goodfellow doing battle with the Evil Black Baron for the hand of the lovely Trudy Truelove.

A replica of the real Red Baron’s tri-plane, the D-7 Fokker, one of WWI’s most advanced planes, still flies. But the Camel is now grounded due to age.

Rebuilding Spirit of St. Louis at Rhinebeck Aerodrome

Several planes are original, but most are painstakingly researched replicas, reconstructed right on site. Besides watching air-shows, visitors can see these planes in the process of being built.

Aerodrome pilot and mechanic, Ken Cassens is finishing up an exact replica of The Spirit of St. Louis (the original is in the Smithsonian). The Spirit made headlines as the plane that flew the first solo-nonstop flight across the Atlantic, piloted by Charles Lindbergh.

Adventurous types might want to get up in the air. Should you wish, you can fly in one of these open-cockpit bi-planes – with an experienced pilot, of course. Check website for Aerodrome’s opening and closing dates and hours, entry fees, and to sign up for a ride. In 2024, rates were $150 per person for a 15 minute ride, two passenger minimum in a four passenger plane.

Wildenstein, Rhinebeck NY

VISIT: Wilderstein Historic Site

This fanciful Queen Anne-style country home, Wilderstein, commands a Hudson River School of Art view of the venerable river. You can take a tour or just roam the gorgeous grounds for free.

From the website – “The last resident of Wilderstein was Margaret (Daisy) Suckley. A cousin and confidante of Franklin D, Roosevelt, Miss Suckley traveled extensively with FDR during his presidency, gave him his famous black Scottish terrier Fala and helped to establish his library in Hyde Park. Miss Suckley was with FDR when he was fatally stricken at Warm Springs, Georgia in 1945. She died at Wilderstein in 1991, in her 100th year.

The letters they exchanged during their friendship, discovered in a black battered suitcase at Wilderstein, provide one of the best resources for understanding the private side of Roosevelt’s life during his presidency.” Tours May-Oct, Check website for tour costs and times.

Montgomery Place

VISIT: Montgomery Place

A few miles north of Rhinebeck, you’ll find the former residence of Janet Montgomery, who built and owned  Montgomery Place in the late 1770’s. Widowed at a young age, she eventually purchased and ran a working farm later in life – quite unusual for a woman of those times.

Since her death in 1844, seven generations of the family lived here until 1986 when the home and 400 acre grounds were turned over to Historic Hudson Valley.

In 2016, Montgomery Place became part of Bard College. Still, it perpetuated the original owner’s intent to promote “pleasure walks through the woods,” leaving the sculpture-studded grounds open to the public. Bard also opens their door to the public for its programs and exhibitions. So, check the website when you’re in town.

Poets Walk Park

WALK: Poet’s Walk

This tranquil 2 ¼ mile Poet’s Walk on paths along the Hudson brings you through fields and woodlands with vistas of the riverfront. Certainly, “a landscape that inspired 19th century writers.” Glorious.

Periwinkles of Rhinebeck

SHOP: Periwinkles at Rhinebeck

The women-owned Periwinkles at Rhinebeck sells crafts by local artisans, dog treats, handmade soaps and lotions, and perfect natural Bug Sprays for hikers who can’t stand mosquitoes. A great little shop.

SHOP: Boutiques And Stores on Market Street

Most art galleries and boutique shops can be found on Market Street. Browse the afternoon away.

Upstate Film, Rhinebeck NY

SEE: Upstate Film Theater

Rhinebeck’s indie/arts movie house, Upstate Film Theater, features the hottest indie films out there.

CLIMB: Fire Tower at Ferncliff Forest

There are 12 miles of hiking trails in Rhinebeck’s Ferncliff Forest – a free to the public venue for your daily dose of Forest Bathing and other outdoor activities. But the nature preserve’s 80-foot fire tower is its prime attraction, as the tower affords tantalizing and timeless Hudson River vistas from its tippy-top viewing platform. Free, open daily dawn till dusk.

SHOP: Rhinebeck Farmers Market

Henry Hudson deemed the Hudson Valley, “the finest land for cultivation I’ve ever set foot on.” So, it’s no surprise to find that this is one of the most productive and indie-owned agricultural regions in the country. In fact, there are nearly 5,300 small and medium sized farms counties that border the Hudson River. Some of these farms sell their produce and meats at the Rhinebeck Farmers Market that runs every Sunday from mid-May to mid-December. Plan to drop by and stock up before heading back home.

Omega Institute for Holistic Studies, Rhinebeck, NY. eOmega.org

LEARN: OMEGA Institute

According to its brochure, Omega is “the nation’s most trusted source for wellness and personal growth programs.” Many people consider a stay there “a spiritual awakening”.

Best Places to Eat and Drink in Rhinebeck NY

EAT: Bia-Rhinebeck

The cosy Bia-Rhinebeck has been winning raves with its innovative and mouthwatering comfort food since it opened. From Irish Stout Brown Bread to Venison Schnitzel, and great cocktails, you’ll find something to your liking. Plus, more importantly, Bia stayed busy and paid their staff through the pandemic, with private outdoor tents that one diner said made her feel like “Arabian royalty.”

Fosters Coach House Tavern, Rhinebeck

EAT: Foster’s Coach House Tavern Rhinebeck NY

Historic, dark and clubby, Foster’s Coach House Tavern opened in 1890 and often gets overlooked by tourists now. But locals have not abandoned it. Food is good and basic. Service is friendly and attentive. Go for the experience of dining on traditional fare, basic burgers, and French Dip in old horse stalls.

EAT: Locals Also Recommend

The Amsterdam for cocktails and “elevated farm to table” fare. Matchbox Cafe for burgers. Pizzeria Posto for “best pizza.” 

Where to Stay Rhinebeck NY

Whistlewood Farm, Rhinebeck NY

STAY: Whistlewood Farm

As you enter the driveway past pastures dotted with grazing horses, you realize Whistlewood Farm is not the typical over-upholstered B&B. It’s country-chic as inspired by Ralph Lauren.

An antique cook stove in the well-used kitchen serves as the baked-goods shelf – with homemade sweets available 24 hours a day.

Owner Maggie Meyer prides herself on the Strawberry, Rhubarb, Apple, and Pumpkin pies that emerge hot from her oven. Not to mention the full country breakfast served every morning.

An open fire pit – eight feet across – draws guests outside, as does miles of woodland trails on the property.

STAY: Mirbeau Inn and Spa

Newly opened, Mirbeau Inn and Spa has oodles of traditional charm, and provides a swanky guest experience.

STAY: Beekman Arms Hotel

The Beekman Arms Hotel has been welcoming visitors for over 250 years, so apparently owners know how to make guests happy. If you’re looking for a historic stay – this is your inn.

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  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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