Adventures

The estate of the Livingston family offers gorgeous grounds with Hudson River and Catskill Mountain views, a formal garden, and wide open lawn for kids to run. Free to walk the grounds. The historic mansion is open seasonally for tours.

All ages · Open, mostly flat grounds

A 190-acre community forest with well-marked trails through towering hemlocks, a stone fire tower you can climb for sweeping views, and a small pond. One of the most beloved local hikes — great for all ages. Dogs welcome on leash.

All ages · Fire tower climb requires some scrambling

A 330-acre state park with forested trails, Hudson River frontage, a marina, and picnic areas. The Blue Trail follows the river bluff for beautiful water views. Connects to Staatsburgh State Historic Site. Great for a longer hike with kids.

All ages · Moderate terrain

The historic estate of Hudson River School painter Frederic Church features miles of carriage roads and paths designed as a living landscape painting. Free to walk the grounds anytime — explore meadows, a lake, and iconic Hudson River views. The house tour is ticketed; the trails are always free.

All ages · Mostly gentle carriage roads

A 120-acre Scenic Hudson park with easy, wide paths through meadows and cedar groves to three dramatic overlooks of the Hudson River and Catskill Mountains. Rustic cedar pavilions dot the trail. One of the most beautiful easy walks in the region — stroller-accessible on the main path.

All ages · Main path stroller-friendly

One of the last intact tidal wetland systems on the Hudson, Tivoli Bays offers peaceful trails through marshes, upland forest, and shoreline. Prime birdwatching — bald eagles nest here. A hidden gem perfect for nature-curious kids.

All ages · Flat and easy

A beloved Hudson Valley farm with pick-your-own strawberries in June, blueberries in July, tomatoes in August, and apples & pumpkins in fall. The farm market, bakery, and art barn make it a full day out. One of the best PYO destinations in the region.

All ages · Young kids love strawberry season

One of the region's most celebrated farms, Migliorelli has a roadside stand in Tivoli and is a fixture at NYC greenmarkets. Stop in for fresh sweet corn, heirloom tomatoes, peaches, and more at their local stand. A great way to experience Hudson Valley farming at its best.

All ages

Set on the grounds of the historic Montgomery Place estate, this orchard opens for U-pick apples in fall with gorgeous river and Catskill views. A magical setting for apple picking — one of the most scenic farms in the Hudson Valley.

All ages

A small family farm tucked up a country road, Thompson-Finch is famous for its U-pick blueberries in July and August. The farm grows more than 20 varieties across a gorgeous hillside setting. One of those special local spots worth the drive.

All ages · Toddlers love the low blueberry bushes

Bard College has a gorgeous open campus you can freely explore — including the iconic Frank Gehry-designed Fisher Center for the Performing Arts. Wander the trails along the Hudson, visit the gardens, and take in the architecture. Free to explore on foot.

All ages

A one-of-a-kind open-air museum of early aviation with a collection of WWI-era planes, barnstorming airshows on summer weekends, and biplane rides over the Hudson Valley. Kids go absolutely wild for it. Airshows run June through October.

All ages · Best for kids 4+

The opulent 79-room mansion of Ruth Livingston Mills, built in 1895 by McKim, Mead & White. Free tours of the grounds year-round; mansion interior open seasonally. The river-facing lawn is stunning and free to explore anytime.

All ages

A beautifully preserved Queen Anne mansion with sweeping Hudson River views, 19th-century landscape gardens, and guided tours of the interior. The grounds are serene and picnic-friendly. A hidden gem tucked along the river in Rhinebeck.

All ages · Grounds always open

A town-maintained swimming area popular with local families for its calm water and shaded picnic spots. A low-key alternative to a crowded pool — bring a lunch and spend the afternoon.

All ages · Great for young children

A full-service state park with two sandy swimming beaches on Lake Taghkanic, rowboat and kayak rentals, picnic pavilions, and hiking trails. One of the best family beach days in the region — about 20 minutes from Rhinebeck.

All ages · Lifeguards on duty in season

The town's outdoor public swimming pool, open to residents and visitors throughout the summer. Swim lessons, lap lanes, and a wading section for little ones. Season typically runs late June through Labor Day.

All ages · Wading area for toddlers

A paved rail trail running through the heart of Dutchess County, perfect for family bike rides, jogging, and walks. The northern section passes through beautiful farmland near Rhinebeck. Flat, easy, and well-maintained — great for kids on bikes or in trailers.

All ages · Perfect for kids' bikes and trailers

A self-guided, mostly flat bike ride through Rhinebeck's historic village streets — past the Beekman Arms, the village green, and along quiet residential roads. Great for introducing kids to road cycling. Pick up a village map at the Visitor Center.

All ages · Best for kids 5+ on their own bikes