This time last year, we pulled together a list of 2025 exhilarating bucket list activities to do in the mid-Hudson Valley.
But for our 2026 list, we decided to do it a bit differently.
We’ve curated local experiences that allow you to be a tourist in your own town, and for a couple on this list, they cost nothing besides the gas money to get there.
This bucket list is an endeavor to be within budget, while local-minded at heart, focusing on those area opportunities many say they want to do each year, but just don’t get around to it.
Read on for the list, but if you think we’ve missed any, you’ve got the chance to submit your own ideas too.
Mid-Hudson Valley 2026 bucket list:
Take a local cruise for dinner, sightseeing
If getting out on a boat in 2026 is on your bucket list, you don’t have to go far to find an opportunity to set sail with the Hudson River nearby.
Charter a sunset cruise with Tivoli Sailing Company, from Rhinecliff or Kingston, or with Nothing But Time Sailing Charters in Poughkeepsie.
With R.M.S. Cruises, out of Peekskill, you can hop aboard a ship and become a tourist in your own town or host a spectacular private special event.
Join Hudson River Sloop Clearwater, situated in Beacon, for a “sailing classroom” educational experience, according to their website, or try one of their public sails, get a private charter, or have your next corporate event on the water.
Locals can venture to take a cruise from Beacon with a destination in mind from Bannerman Castle Trust. It’s a 30-minute ride on the water to get to the historical Bannerman Island, where residents can take a guided walking tour to see the Bannerman Castle ruins and gardens. There’s plenty of other experiences to be had, from movie nights to walking and kayaking tours, along with self-guided tours with live music.
With Hudson River Cruises, based in Kingston, take a sunset sightseeing cruise, listen to live music on another cruise, host a private event, set up a group tour or even a school field trip.
On Solaris, a 100% solar-powered cruise boat, get unique views as part of the Hudson River Maritime Museum in Kingston. Set sail on a lighthouse tour, dual lighthouse cruise, sunset cruise, live music cruise, sightseeing cruise and historical cruises. Believe it or not, there’s also a meditation cruise.
Lastly, with New York Boat Co.’s Kingston location, on the Stroller IV, book a fall foliage or sunset cocktail cruise. Private charters are available, too, for both their Kingston and Peekskill launches.
Run a marathon or dabble in a race
Looking to train for and run a marathon in 2025? There are five opportunities in the mid-Hudson Valley to take advantage of:
Although if a marathon might be too much, here are some 2026 5Ks — some have walks — to gear up for:
Discover mid-Hudson Valley’s Wineries
With New York’s Hudson Valley home to the oldest winery in America — Brotherhood Winery in Washingtonville, Orange County — as well as allegedly having the oldest vineyard in the country, according to Benmarl Winery, taking a day to explore what experiences the area has to offer may be on your 2026 bucket list.
Across Dutchess, Ulster, Orange and Sullivan counties, you’ll find over 20 wineries, so there’s no shortage of options.
But, if you’re looking to narrow down your search, try these wineries in Dutchess below or try Dutchess Tourism’s Dutchess Wine Trail.
If you’re closer to Ulster and Orange counties, the Shawangunk Wine Trail, comprised of 13 wineries, might be the place to start. Otherwise, you can check out these Ulster and Orange County wineries below, and find the ones closest to you.
Ulster County wineries:
Orange County wineries:
For those in Sullivan County or visiting the area, check out Bashakill Vineyards, nestled on a wetland preserve in the Catskills, for an intimate wine experience.
Albeit, if cideries, breweries or distilleries are more your speed, you could try iloveny.com/things-to-do/food/cideries-and-distilleries/ to find one near you.
Renaissance Fair: take a trip back in time
Immerse yourself in the realm of the New York Renaissance Faire, situated at 600 state Route 17A, Tuxedo, in Orange County, in late summer and early fall of 2026.
The faire, which typically runs from mid-August to early October, will be back again next year, according to the New York Renaissance Faire Instagram. With people gearing up in armor and costumes, and themed weekends for inspiration, it feels as though you’re transported to the era.
There is something for everyone, including plenty of entertainment, vendors with artisan crafts and wares, pubs and eateries scattered throughout, as well as games and rides to enjoy on a day at the fair.
Check back on their website, renfair.com/ny/, as the event gets closer for more specifics, but in the meantime, visit their site to learn more.
Go on hot air balloon ride
With the Hudson Valley Hot Air Balloon Festival situated in Union Vale’s Tymor Park, in Dutchess County, taking flight may only be a short drive away.
At the festival each year, by the Dutchess County Regional Chamber of Commerce, participants can go for a full flight in the morning or evening, or for a tethered flight.
2026’s event, during Labor Day weekend, from Sept. 4-6, will mark the festival’s 35th anniversary.
However, with this being many months out, there aren’t a lot of details out for next year’s programs. In the meantime, mark your calendars and check back with their Facebook page, facebook.com/HVBalloonfestival/, or website, dcrcoc.org/balloonfesthv-org/, as the festival gets closer, for more information.
Since the event is still months away, there aren’t too many details available, but mark your calendars and remember to check back with their Facebook page, facebook.com/HVBalloonfestival/, or website, dcrcoc.org/balloonfesthv.org, as the festival gets closer, for more information.
Discover the mid-Hudson Valley’s major historical sites
The area’s historic sites are not only a great place to learn more about the history of where you live, but also tend to have innovative events and breathtaking views, from views of the Hudson River to historic architecture and even fairy-tale like gardens.
Here’s five major historical sites from Dutchess, Ulster, Orange and Sullivan counties you might want to put on your bucket list to visit in 2026.
Dive into Dutchess County history:
Immersive yourself in Ulster County history:
Engage with Orange County history:
Delve into Sullivan County history:
If you’ve already been to these historic sites in Dutchess, Ulster, Orange and Sullivan counties, try visiting destinationdutchess.com/go/rethink, visitulstercountyny.com/plan-your-visit/things-to-do/category/historic-sites/, pickocny.com/explore-orange-county-ny/history/, and sullivanny.gov/Departments/ParksRecreation, respectively, for more history and sightseeing opportunities.
Hike the largest peaks in the mid-Hudson Valley area
If you’re looking to take on a local hiking challenge in 2026, check out some of the highest peaks in the mid-Hudson Valley area below.
See just how high you can climb in Dutchess, Ulster, Orange and Sullivan counties, ordered by lowest to highest elevation.
Share your ideas for a mid-Hudson Valley bucket list
We want to know your favorite things to do in the mid-Hudson Valley, too.
Have something you think could be bucket list worthy? Send your suggestions to reporter Nickie Hayes at NHayes@poughkee.gannett.com with the subject line “BUCKET LIST” for the opportunity to help shape a community-driven list.
Nickie Hayes is the Breaking & Trending News Reporter for the Poughkeepsie Journal and focuses on how to make the most of what the mid-Hudson Valley has to offer. Contact reporter Nickie Hayes: NHayes@poughkee.gannett.com, 845-863-3518 and @nickieehayess on Instagram.
This article originally appeared on Poughkeepsie Journal: 7 mid-Hudson Valley bucket list items for 2026
Reporting by Nickie Hayes, Poughkeepsie Journal / Poughkeepsie Journal
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