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Here's What to Do in Dutchess County During Vassar and Marist College's Family Weekend

Date Published: August 30, 2022

Family Weekend is just around the corner for Vassar College and Marist College! September 30-October 2 is your opportunity to explore Dutchess County. Read on for hidden-gem hikes, apple and pumpkin picking, craft beverage destinations, top free things to do and activities for every generation of the family.

Have questions about planning your trip to Dutchess County? Call us at 845-463-4000

Hikers exploring fall Bannerman Island
Bannerman Island, Beacon


New York Cider Festival is an 11-day celebration of the thriving state-wide craft cider industry, running Sept. 29-Oct. 9. Sample some of the best of Hudson Valley cider just as the fall season begins!

Friday, Sept. 30 features several fun events just a short drive away from Poughkeepsie college campuses. Visit the center of Rhinebeck for the Music on Market Concert Series. Or, head down to Beacon and enjoy an evening tour of Bannerman Island followed by a screening of "The Hunchback of Notre Dame." In addition, Downton Abbey fans can take a themed Staatsburg State Historic Site tour highlighting lives of the elite in the post-Edwardian era as well as The Gilded Age.

Saturday, Oct. 1 is the perfect day to catch an air show at Old Rhinebeck Aerodrome. Or, head to Bowdoin Park in Wappingers Falls for the Hudson Valley Gospel Festival, which includes choir and dance performances set against the backdrop of the river. 

Finally, Sunday Oct. 2 relax at Millbrook Vineyards and Winery for picnics fueled by local food trucks. For more Dutchess County events, click here

Bundle of apples at Fishkill Farms
Fishkill Farms, Hopewell Junction

Pick-Your-Own Apples, Pumpkins and More at These Dutchess Farms

Few destinations in the world are more iconic for autumn than the Hudson Valley. Luckily for parents during Family Weekend, Dutchess County has several farms and orchards open for apple and pumpkin picking. Enjoy fruit fresh off the trees, dig into the region's famous cider donuts and get the cutest fall photos with the family. For pick-your-own apple orchards, click here. 

Poets Walk Park
Poets' Walk Park, Red Hook; Photo by Marist alumn Zachary Gawron

Top 10 Free Things to do in Dutchess County 

Dutchess County has many completely FREE activities that are excellent experiences for families. Hike Peach Hill Park in Poughkeepsie, discover classic art at Francis Lehman Loeb Art Museum and contemporary works at the Wassaic Project, stroll through our Great Estates and more! For the full top 10 list of free things to do in Dutchess, click here. 

Women enjoying Zeus Brewing Co rooftop
Zeus Brewing Company, Poughkeepsie

Use Your Dutchess Tourism Taste Finder Passport to Sip and Save in Style 

Any craft beverage fans in the family? Select a 1-day or 3-day pass for all 21+ members of the family to score free tastings, merch and more at your choice of 13 Dutchess County hotspots. Spend time at breweries, cideries, wineries, distilleries and meaderies, several of which are located on breathtaking farms! In fact, Poughkeepsie itself is home to several producers on the list, including Slate Point Meadery, Plan Bee Farm Brewery and Zeus Brewing Company. For the full list of destinations on the Taste Finder craft beverage passport, click here. 

Related: The Dutchess Tourism Trail Finder is a mobile passport program featuring attractions, experiences, and can’t-miss sights throughout the region. For your convenience, they’re presented in four carefully crafted trails, each catering to a distinct set of interests. To find the perfect trail for you, click here

Kitchen and Coffee
Kitchen+Coffee, Beacon; Photo by @anjueatsfoods

Top 10 Eateries for Vegetarian and Vegan Diners

Searching for restaurants that have vegan and/or vegetarian options? Luckily, Dutchess County hosts dozens of vegan-friendly eateries. For those with dietary restrictions, every meal of the day is covered by our top 10 list. From farm-to-table cafe fare and smoothie bowls to authentic Indian and Thai, there's something for everyone's palate. For vegetarian and vegan dining, click here. 

Old Rhinebeck Aerodrome biplane ride
Biplane ride at Old Rhinebeck Aerodrome, Red Hook

Top 10 Activities for Every Generation of the Family 

Visiting with a multi-generational family? We have plenty of experiences for groups of all ages. Fascinating historic sites, bucolic farms and breathtaking brunch spots overlooking the Hudson River are on the table. Plunge into the lives of the Roosevelts at the FDR Presidential Library & Museum, watch WWI biplanes soar over Red Hook (or take a ride in one yourself), stroll across a Chinese and Japanese-inspired landscape at Innisfree Garden and more! For our top 10 activities for every generation to do together, click here. 

Plus, download our FREE Connection Finder family fun trail for deals and discounts. Visit alpaca farms, bring the little ones to climbing gyms and trampoline centers, enjoy ice cream made with local dairy and catch late-season flicks at a retro drive-in theater. To download your passport, click here. 

Dog at Vanderbilt
Vanderbilt Mansion National Historic Site, Hyde Park; Photo by @heytherestan

Dog-Friendly Jaunts in Dutchess 

Wondering where you can go and bring along your pup in Dutchess County? Here’s a few of our dog-friendly hiking trails, historic sites, craft beverage hotspots and more in the Hudson Valley!

Top 10 Hidden Gem Hikes 

Late September is one of the best times of the entire year to go hiking in the Hudson Valley. Get ready to traverse tranquil trails! Choose from our list of under-the-radar destinations for peaceful jaunts into nature. Conquer these upward paths for stunning views of the Catskill Mountains, Berkshires and Hudson Highlands. For 10 stellar outdoor experiences, click here

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