10+ Things to do in Rhinebeck NY | Dutchess County NY

8 min readNov 1, 2020

Dutchess County NY presents a multitude of possibilities to every type of visitor. Rhinebeck NY is at the heart of this large and diverse county.

With so many things to do in Rhinebeck NY, how do you decide what’s best for you?

Since visiting Rhinebeck NY with my teenage daughter, I have come to the conclusion that this town should not be missed during a visit to Dutchess County NY.

It may seem ‘out of the way’ to some, but after driving along Route 9 through some of the most historic places in the Hudson Valley, one cannot take away the beauty of this small town.

This type of outing will inspire and educate. With so many things to do in Rhinebeck NY, how can someone be bored?

Visiting Rhinebeck NY:

Where is Rhinebeck NY?

Before I get into the specifics of Rhinebeck NY, you’re probably wondering where it is exactly.

Rhinebeck NY is located in Dutchess County, approximately 30 minutes north of Poughkeepsie and the Mid-Hudson Bridge.

The easiest way to get to Rhinebeck NY is with a car and there are several options: the New York State Thruway, the Taconic State Parkway and/or Route 9.

Located approximately 110 miles north of New York City and approximately 51 miles south and east of Albany NY through the New York State Thruway (I-87) and over the Kingston-Rhinecliff Bridge. That makes the trip between 2–3 hours depending on the day/time you’re traveling.

About Rhinebeck NY

Of all the towns in Dutchess County, Rhinebeck NY feels a little more touristy. Due to hosting the Dutchess County Fair (cancelled for 2020) and with an abundance of things to do, Rhinebeck NY is full of amenities and hotels for those staying in town.

It’s also the place most likely to attract the type of tourist who might just be going for a long weekend. For many people that might mean it’s an easy destination to travel to. For others, they might be looking to get away from the crowds of city life.

Known mainly for the Dutchess County Fairgrounds and the Old Rhinebeck Aerodrome, Rhinebeck NY is also home to historic homes and so much more. With over 400 registered historic landmarks in the area, this makes Rhinebeck a town chock-full of history and a place where you can stay busy for a long time.

In general, there are many things that attract people to Rhinebeck NY, including arts, history, food and outdoor activities. Honestly, this small town in Dutchess County NY has something for everyone.

For more information about the town itself, visit the official town website: enjoyrhinebeck.com

Things to See & Do in Rhinebeck NY

#1: Dutchess County Fairgrounds

Home of the Dutchess County Fair and other special events, this fairgrounds began hosting the annual Dutchess County Fair in 1919.

In addition to having the responsibility of hosting the largest agricultural six-day fair in New York, the fairgrounds also hosts:

Craft Shows
Antique Shows
The Sheep & Wool Festival
Livestock shows
The popular Wine & Food Festival

#2: Shop at Businesses on Market Street & Montgomery Street

During our visit to Rhinebeck NY, we went for one thing and one thing only: To visit Samuel’s Sweet Shop!

Samuel’s Sweet Shop is owned by actors Paul Rudd & Jeffrey D Morgan. When Samuel’s was in jeopardy of closing, these two locals stepped in and saved this Rhinebeck institution. Loaded with new candy, vintage candy, candy from all over the world and delicious chocolates.

Known for it’s amazing coffee, it’s best paired with pastry or a rice krispie treat topped with a photo of Paul or Jeffrey!

Other local favorites shops include:

Oblong Books & Music — located on Montgomery Street, this book lover’s heaven is open to the public on select days and offer curbside pick-up on the days they are not physically open (Tues & Wed). Offering an extensive collection of books for adults, young adults and children, Oblong is the place to go when you need a book.
A.L. Stickle — located on East Market Street, A.L. Stickle is what good old-fashioned variety stores are made of. A landmark of Rhinbeck NY since 1946, this is a true “5 and Dime” shop. Their tagline says it all: “Shop in 2020 like it’s the 1960's”.
Winter Sun and Summer Moon — Located on East Market Street, Winter Sun & Summer Moon showcases clothing, gifts, jewelry, handcrafts & personal care from around the world and also sourced locally. It’s a quaint little shop that offers a nice variety of eclectic and beautiful products.

#3: Visit the Old Rhinebeck Aerodrome

America’s first flying museum of antique aircraft, the Old Rhinebeck Aerodrome is a popular destination for many. With an array of vintage aircraft, antique cars and motorcycles, the museum typically offer air shows on the weekends (cancelled for 2020).

They also offer biplane rides on a first come — first serve basis on weekends and by reservation. Open seasonally, this is a great place to visit during the warmer months.

#4: Eat at one of the many Rhinebeck NY Restaurants

Boasting a large selection of cuisines, Rhinebeck NY is a great choice for dining.

Here are some popular Rhinebeck NY restaurants:

The Amsterdam — Located on Mill Street, this great restaurant is open for lunch and dinner. The Amsterdam is both a wonderful restaurant and market. This unique combination makes it a popular restaurant in Rhinebeck.
Terrapin — Located in an almost 200 year old church, Terrapin is not only in a unique setting, it also serves as a grand example of farm-to-table dining in the Hudson Valley. Their Bistro is set for casual dining while the restaurant offers a fine dining experience anyone can enjoy.
Gigi Hudson Valley — Serving the best of the Mediterranean and the Hudson Valley, Gigi’s outdoor patio is a perfect place to spend an afternoon while enjoying a divine meal. Open for lunch & dinner everyday except Monday, this is a local favorite.
Market St. — Known for it’s wood burning brick oven serving Neapolitan-style pizza, Market St. is a favorite amongst locals and visitors. Their menu showcases contemporary Italian cuisine serving the freshest and finest ingredients.
Foster Coach House Tavern — This landmark of Rhinbeck NY has been around since 1890. With so much history in one place, it’s no wonder it is a favorite of local and visitors alike. Serving up American cuisine, this is the perfect place to create lasting memories.

#5: Rhinebeck Farmer’s Market

If you love farmer’s markets as much as I do, a visit to the Rhinebeck Farmer’s Market is a must. Taking place every Sunday from May through December, the market takes place rain or shine and is a beloved event that people enjoy.

#6: Support Rhinebeck’s Upstate Films from home

Although this icon of films is closed for screenings, they offer a program called, “Upstate Films Virtual Cinema”. Specializing in indie films & documentaries, Upstate Films is a local attraction that is missed and will hopefully return soon.

Purchase a ticket for a movie and watch it from the comforts of your home. After purchasing a ticket, you 4 days to watch the film at home. Trailers are also available on the website.

#7: Visit Wilderstein Historic Site

With spectacular views of the Hudson River, Wilderstein is open for outdoor tours (2020 season) by reservation online. Typically, guided tours of the inside of the historic home are offered, but have been cancelled at this time.

This majestic home is an elaborate Queen Anne-style mansion and have been occupied by three generations of the Suckley family. The expansive 40-acre grounds are open to the public to enjoy.

#8: Take a hike in Ferncliff Forest or Burger Hill

With impressive views of the Hudson River Valley, a climb to the top of the Ferncliff Forest Fire Tower is a must for anyone who is not afraid of heights. The forest is open year-round for walking, hiking, mountain biking, fishing, and more.

The panoramic views at the top of Burger Hill can’t be beat. If climbing the fire tower at Ferncliff Forest is not your cup of tea, then a trip to Burger Hill may be a better choice. The views at the summit are outstanding and I’ve heard that Burger Hill is an epic sledding area.

#9: Spend the Night at One of the Historic Inns

Olde Rhinebeck Inn — A true Rhinbeck NY institution, one may think that they’d be plenty of stories told of this place. Serving Rhinebeck and the surrounding areas sine 1745 is no easy feat, but the Olde Rhinebeck Inn still stands and as busy as ever. This majestic farmhouse is a Best & Breakfast that people only dream of.
Beekman Arms Inn — Within the Rhinebeck Village Historic District sits ‘America’s oldest continuously operated hotel’. This traveler’s Inn was established in the early 1700’s and has been sitting at its present location since 1766. It has hosted many leaders of the American Revolution, including George Washington, Philip Schuyler, Benedict Arnold and Alexander Hamilton.

#10: Pick your own flowers at Brittany Hollow Farm

This seasonal activity is a must for those just wanting peace and tranquility while picking your own flowers. The wildflowers are abundant and for a fee, you pick a bucket full of your own flowers. The best part is that you can keep your bucket and return and pick more another day for a reduced rate. This is a unique way to spend the day in Rhinebeck NY.