Westchester

Day Trips

Make the most of your day with our curated plans, packed with Westchester's hidden gems and unique experiences!

day 1
Scenic Start in Westchester
morning
:

Begin your day at the beautiful Kykuit, the Rockefeller estate, and explore its meticulously manicured gardens. Don't forget to take a guided tour to learn about its rich history.

afternoon
:

Head over to the Philipsburg Manor for a glimpse into colonial life along the Hudson River. Enjoy a leisurely lunch in the charming town of Tarrytown.

evening
:

Conclude your day with a sunset view at the Tarrytown Lighthouse. Dine at one of the local restaurants offering diverse cuisines.

day 2
Active Adventures in Westchester
morning
:

Rent a bike and ride through the scenic bridle paths of Rockefeller State Park Preserve. Enjoy the tranquility of nature as you pedal along beautiful trails.

afternoon
:

Stop for lunch at a cafe in Pleasantville before visiting the Jacob Burns Film Center for an afternoon screening. Engage with the local film community.

evening
:

Join a fitness class or outdoor yoga session at one of the parks. Finish your evening with a refreshing smoothie at a nearby health food cafΓ©.

day 3
Artsy Explorations in Westchester
morning
:

Start your day at the Neuberger Museum of Art, enjoying various contemporary art pieces. Participate in any morning workshops that might be available.

afternoon
:

Visit the historic town of Chappaqua for lunch, followed by browsing local galleries and boutiques. The artistic vibe of the area will surely inspire you.

evening
:

Experience a live music event or theater production at the Caramoor Center for Music and the Arts. Cap it off with dinner at a fine dining restaurant.

day 4
Wine and Dine in Westchester
morning
:

Kick off your day with a visit to one of the local farmer's markets for fresh produce to take home. Take a stroll through the picturesque surroundings.

afternoon
:

Tour a local winery in the Hudson Valley and indulge in wine tastings. Enjoy a relaxing lunch at their bistro with scenic vineyard views.

evening
:

Dine at a farm-to-table restaurant to savor seasonal dishes paired with wines from the region. Wrap up with a cozy night at a nearby boutique hotel.

day 5
Nature Retreat in Westchester
morning
:

Visit the stunning Croton Gorge Park, where you can hike and enjoy breathtaking views of the dam. Bring a camera to capture the beauty of the surrounding nature.

afternoon
:

Enjoy a picnic lunch there before heading to the nearby Teatown Lake Reservation for more hiking and wildlife watching. Interact with nature center exhibits to learn about local ecosystems.

evening
:

End your day with stargazing at Teatown, where volunteers may host public events. Enjoy a relaxed dinner at a local cafe afterward.

day 6
River Adventures in Westchester
morning
:

Kickstart your day with kayaking on the Hudson River; equipment can be rented from local outfitters. Enjoy the picturesque waterway as you paddle along.

afternoon
:

Savor a riverside lunch at a local seafood shack while watching boats go by. Spend your afternoon exploring nearby waterfront parks.

evening
:

Join a sunset cruise on the Hudson for breathtaking views of the river and surrounding landscapes. End the night with dessert at a charming waterfront cafΓ©.

day 7
Historical Journey in Westchester
morning
:

Start the day with a guided tour of the famed Wave Hill, a public garden and cultural center in the Bronx. Appreciate the rich history while enjoying the gardens.

afternoon
:

Visit the Old Croton Aqueduct State Historic Park for a historical hike. Pack a lunch to enjoy along the scenic route.

evening
:

Explore the historical sites in Bronxville and dine at a local eatery. Take a leisurely stroll after dinner to appreciate the town's charming architecture.

day 8
Shopping Spree in Westchester
morning
:

Devote your morning to shopping at The Westchester Mall, which features various high-end stores. Enjoy browsing through fashion, tech, and home goods.

afternoon
:

Grab lunch at one of the mall's gourmet food options before heading to nearby boutiques in White Plains. Take your time exploring unique finds.

evening
:

Catch a movie at the mall's luxury cinema for a relaxed evening. Wrap up with dinner at a trendy restaurant in the area.

day 9
Family Fun in Westchester
morning
:

Visit the interactive exhibits at the Westchester Children's Museum to kick-start a fun family day. Kids will be thrilled with hands-on activities.

afternoon
:

Have lunch at a family-friendly eatery, then spend the afternoon at Playland Park, enjoying the rides and games. Create lasting memories together.

evening
:

End the day with ice cream at a local parlor and a stroll along the beach. Share stories of your adventures and enjoy the warm night air.

day 10
Outdoor Excursion in Westchester
morning
:

Start your adventure with a visit to the Bronx River Reservation and explore its trails. Enjoy a morning of biking or hiking along the river.

afternoon
:

Pack a lunch and enjoy it at one of the scenic rest spots along the trail. Consider renting a canoe or paddleboard for some time on the water.

evening
:

Wrap up your day with a barbeque at one of the parks' picnic spots. Enjoy quality time with friends or family surrounded by nature.

Discover Westchester

Read more in our Westchester 2024 Travel Guide.

Westchester Travel Guide