10 Reasons to Visit Dutchess County, New York

A trip to downstate New York can offer a quick escape; with beautiful natural surroundings, charming towns, farm to table dining, wineries, and more.
If you plan your trip in advance, you can also catch some of the local festivals and concerts that happen in New York’s Dutchess County.

Here are the top 10 Events in Dutchess County:

1. March – St. Patrick’s Day Parade. Held on first Saturday in March, each year the Committee selects an outstanding community person to lead the parade who is the Grand Marshal.
2. April – Wappinger Creek Water Derby. Who says you need to get to the Caribbean to scuba dive? Take lessons, compete in canoe races, and more, right here in New York.
3. May – Rhinebeck 2016 Antique Car Show & Swap Meet. Check out antique and classic cars on display at this 3-days long car show.
4. MayWW II Living History, USO Show, Bivouac, and Memorial Day Events include the 75th Anniversary of FDR Presidential Library & Museum and Home of Franklin D. Roosevelt National Historic Site, and 100th NPS anniversary.
5. June – Country Living Fair, Rhinebeck. This weekend-long fair includes art displays, live concerts,  food tastings, and dozens of themed gardens to keep the entire family entertained.
Dutchess County Fair
Dutchess County Fair
6. June – Discover Hudson Valley Bike Ride. Explore forests, waterfalls, hills, and gorgeous surroundings of the Hudson Valley on a guided bike tour.
7. July – DCRCOC Balloon Festival, Poughkeepsie. Over 100 hot air balloons are launched from the banks of the Hudson River, against the backdrop of a picture-perfect sunset.
Dutchess County Balloon Festival
Dutchess County Balloon Festival
8. August – Jazz in the Valley, Poughkeepsie. An annual festival, showcasing music performed by world-class musicians, fittingly complemented by breathtaking views of the Hudson River Valley as a backdrop.
new york jazz festival
9. September – Hudson Valley Wine and Food Festival & HV Craft Beer Festival. Taste local products including beer, cider, spirits, wine, and food at this weekend-long gastronomic festival.
10. October – New York State Sheep and Wool Festival. Features livestock displays, competitions, art display, cooking demonstrations, and lots of kid’s activities.
Dutchess County festivals
Dutchess County Festivals

To learn more about spending a weekend in downstate New York, read this post by GoEatGive.

~ Information sourced from Dutchess County Tourism. 

Weekend in Hudson Valley Region, New York

Hudson Valley Region, not often is this what comes to mind when I think of New York. When I think of New York, images of the city’s bustling streets, neon lights, Broadway musicals, top chef restaurants, and shopping at 5th Avenue fill up my head.

However, The State of New York is actually incredibly vast and has a lot more to offer than Manhattan and the surrounding boroughs. For the first time, I took a train starting at Grand Central Station to explore the surrounding areas of downstate, New York.

Hudson Valley Region, NY

Hudson River Bridge, Poughkeepsie, Hudson Valley Region, NY
Hudson River Bridge

The Hudson Valley area is roughly 150 miles long and covers various counties. It is easily connected to New York City by train and makes for fun weekend getaways. 

Poughkeepsie, NY

A 2-hour ride on Metro-North Railroad took me along the Hudson River to the city of Poughkeepsie in Dutchess county. A short walk from the train station to the elevator led to the world’s longest elevated pedestrian bridge, spanning 212′ above the Hudson River and 1.28 miles across. This is a great place to get a good view of the river and the surrounding foliage, especially during spring and fall. During the season, there are concerts, open-air movies, marathons, and festivals taking place in the historic state park.

Vanderbilt Mansion in the Hudson Valley Region, NY
Vanderbilt Mansion

Poughkeepsie has several restaurants, hotels, and shops that sustain tourism in the area. Shadows restaurant offers a great view of the Hudson and is often used for large events, such as wedding receptions. Also, nearby is the Franklin D Roosevelt Presidential Library and Museum in Hyde Park.

Here, you can visit the Roosevelt family home, burial site, see the president’s personal library, and an interactive museum. Just a few minutes drives away is the Vanderbilt Mansion, one of the smaller homes owned by the family. After spending an afternoon in the area, you begin to picture what affluence and stature the neighborhood had up until only a few decades ago.

Vanderbilt Mansion Interior, Hudson Valley Region, NY
Vanderbilt Mansion Interior

Food lovers can take a break at The Culinary Institute of America (CIA) for dinner. The oldest and most well known culinary school in the country offers four student-run restaurants. Here when you dine, you will become part of their classroom experience. The CIA’s new 800-seat, state-of-the-art Ecolab Auditorium in the Marriott Pavilion makes it possible for visitors to experience one of Half Moon Theatre’s New York-style theatrical productions after enjoying a meal at The Bocuse RestaurantAmerican Bounty, or Ristorante Caterina de’ Medici.

Rhinebeck, NY

Rhinebeck is a charming city to stay overnight. Check into America’s oldest continuously operated hotel, Beekman Arms, for luxurious accommodations in a historic setting. Next day, stroll around the downtown area, shopping for antiques, clothes, and local products, as well as boutiques and dining at historic taverns. Not to miss is Oliver Kita Confectionaries for hot chocolate, cupcakes, and handmade chocolate truffles. Terrapin Restaurant features farm-fresh organic cuisine under the guidance of award-winning Chef Josh Kroner. There are over 30 wineries in this area and many of them are offered on the menu, paired with locally raised duck, venison, and chicken.

Oliver Kita in Rhinebeck NY, Hudson Valley Region
Oliver Kita in Rhinebeck

Early December is a good time to visit Rhinebeck for the Dutch tradition of Sinterklaas, where a local resident dresses up in a Santa-bishop like attire, accompanied by his long-time sidekick, the Grumpus, as well as the entire town parading through the town.

Overall, the Hudson Valley Region is a historical and culturally intriguing place to explore, just a short way outside of the city!

~This trip was coordinated by I Love New York, the state’s official tourism board.

Read Part 2 of my upstate New York experience in Westchester.