Westchester

Day Trips

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

day 1
Exploring Historic Center
morning
:

Begin your day with a visit to the charming village of Tarrytown, where you can stroll along the picturesque streets lined with historic homes. Stop by the Tarrytown Lighthouse for stunning views of the Hudson River, while learning about its fascinating history. Enjoy a hearty breakfast at a local café, savoring fresh pastries and artisanal coffee.

afternoon
:

Spend the afternoon exploring the renowned Kykuit, the former estate of the Rockefeller family, where you can take a guided tour of the mansion and its stunning gardens. Afterward, head to the nearby Philipsburg Manor, a living history site that offers a glimpse into colonial life along the Hudson River. Don't forget to grab a bite at a local eatery, sampling some delicious regional cuisine.

evening
:

As the sun sets, take a leisurely walk along the Tarrytown waterfront, enjoying the serene ambiance and breathtaking views of the river. Consider dining at a waterfront restaurant, where you can relish fresh seafood while watching the sunset over the Hudson. Cap off your evening with a visit to a local bar for a nightcap or live music.

day 2
Art and Culture in White Plains
morning
:

Start your day in White Plains with breakfast at a local diner, famous for its fluffy pancakes and classic American fare. Afterward, visit the Neuberger Museum of Art, where you can explore its impressive collection of modern and contemporary works. Take in the diverse exhibits, which often feature local artists and thought-provoking installations.

afternoon
:

Spend the afternoon wandering around the bustling downtown area, filled with shops and boutiques that showcase local artisans and crafts. Make sure to stop by the White Plains Farmers Market, where you can sample fresh produce and homemade goods from local vendors. Enjoy lunch at a trendy café, indulging in fresh salads or gourmet sandwiches.

evening
:

As evening approaches, catch a live performance at the White Plains Performing Arts Center, where you can enjoy local theater productions or musical performances. After the show, head to a nearby restaurant for dinner, sampling some international cuisine that reflects the city's diverse culture. Conclude your evening with a stroll through the vibrant streets, soaking in the lively atmosphere.

day 3
Nature Walks and Scenic Views
morning
:

Begin your day with a peaceful hike at the Croton Gorge Park, where you can take in beautiful views of the Croton Dam and the surrounding landscape. Pack a picnic breakfast to enjoy at one of the scenic spots along the trail, surrounded by nature. Look out for local wildlife as you walk the trails, which are ideal for birdwatching.

afternoon
:

Continue your outdoor adventure by heading to the nearby Teatown Lake Reservation, where you can explore the diverse ecosystems and hiking trails. Participate in a guided nature walk to learn about the local flora and fauna, gaining a deeper appreciation for the area's natural beauty. Enjoy a packed lunch at the reservation, taking in the tranquil setting.

evening
:

As the day winds down, return to your accommodations and refresh before heading out for dinner at a rustic tavern nearby. Delight in the farm-to-table offerings that highlight the region's fresh ingredients. Spend your evening relaxing by a fire pit, sharing stories and enjoying the peaceful ambiance.

day 4
Adventure at the Hudson River
morning
:

Kick off your day with an exhilarating kayaking excursion on the Hudson River, where you can paddle along scenic shores and enjoy the fresh air. Join a guided tour that provides insights into the area's ecology and history as you navigate the waters. Afterward, refuel with a hearty breakfast at a riverside café, overlooking the stunning views.

afternoon
:

Spend the afternoon biking along the scenic Hudson River Greenway, where you can enjoy views of the river and the surrounding parks. Stop at various lookout points to capture the beauty of the landscape through your camera lens. Take a break at one of the parks for a leisurely lunch, enjoying the peaceful surroundings.

evening
:

As the sun begins to set, make your way to a local winery for a tasting experience. Sample a variety of wines made from grapes grown in the region, accompanied by artisanal cheeses. Conclude your day with a casual dinner at a nearby bistro, celebrating your adventurous day with delicious food and drink.

day 5
Historic Landmarks and Gardens
morning
:

Start your exploration at the iconic Lyndhurst Mansion, where you can take a guided tour of this Gothic Revival masterpiece nestled in beautiful gardens. Marvel at the architecture and learn about the fascinating history of the estate. Enjoy a light breakfast at the mansion's café, surrounded by lush landscapes.

afternoon
:

Continue your historic tour with a visit to the historic town of Peekskill, where you can explore its charming downtown and visit the Peekskill Museum. Enjoy a leisurely lunch at a local eatery, sampling classic American dishes or fresh farm fare. Afterward, take a stroll along the Peekskill waterfront, with views of the Hudson River and the surrounding hills.

evening
:

As evening falls, return to Lyndhurst to attend one of their seasonal events or outdoor concerts, enjoying live music in a stunning setting. Bring a blanket and picnic dinner to enjoy while you soak in the atmosphere. After the event, head back to your accommodation, reflecting on a day filled with history and culture.

day 6
Family Fun at Playland Park
morning
:

Kick off your family adventure at Playland Park in Rye, known for its historic amusement rides and beachfront access. After enjoying breakfast at a nearby diner, spend the morning riding roller coasters and playing games at the arcade. Capture fun family photos and create lasting memories as you explore the park.

afternoon
:

Break for lunch at one of the park's eateries, where you can enjoy classic amusement park fare like hot dogs and cotton candy. After lunch, continue your fun with miniature golf or a ride on the carousel. Don’t forget to visit the beach area for a chance to relax and enjoy the sun.

evening
:

As the day comes to a close, enjoy a sunset stroll along the beach, taking in the beautiful views of Long Island Sound. Treat the family to dinner at a local seafood restaurant, savoring fresh catches of the day. Wrap up your evening with a visit to the nearby ice cream shop for a sweet treat.

day 7
Exploring Nature Reserves
morning
:

Begin your day early at the Marshlands Conservancy in Rye, where you can enjoy a peaceful walk through diverse habitats and beautiful marshlands. Bring your binoculars for birdwatching as you stroll along the well-maintained trails. Enjoy breakfast at a quaint café nearby, fueling up for a day of exploration.

afternoon
:

After your morning walk, head to the nearby Rye Nature Center for interactive exhibits and educational programs about local wildlife. Participate in a guided nature walk or workshop, allowing your family to learn more about the ecosystem. Enjoy a picnic lunch on the grounds, surrounded by nature.

evening
:

As the sun sets, make your way to the scenic Playland Park for an evening of fun with carnival rides and games. After enjoying the park's attractions, gather for a family dinner at a nearby casual restaurant or pizzeria. End your day with a relaxing family game night back at your accommodation.

day 8
Culinary Delights and Tastings
morning
:

Start your culinary exploration in the heart of Westchester with a visit to a local farmer's market, where you can discover fresh produce and artisanal products. Enjoy a breakfast of seasonal fruits and baked goods from local vendors while mingling with friendly farmers. Gather ingredients for a cooking class later in the day.

afternoon
:

Participate in a hands-on cooking class at a local culinary school, where you can learn to prepare traditional dishes using the fresh ingredients you gathered in the morning. Work alongside a chef to create a multi-course meal, gaining valuable culinary skills. After the class, sit down to enjoy the delicious meal you prepared together.

evening
:

As evening approaches, explore nearby towns to visit some of Westchester's unique restaurants and bars, each offering a distinctive culinary experience. Sample craft cocktails or local wines paired with gourmet dishes prepared by talented chefs. Wrap up your day with dessert at a renowned bakery, indulging in sweet treats that showcase the area's culinary talent.

day 9
Relaxation and Wellness Retreat
morning
:

Begin your day with a relaxing yoga session at a local wellness studio, centered around mindfulness and rejuvenation. Enjoy a light breakfast at a health-conscious café, focusing on organic ingredients and nourishing options. Take some time to explore the nearby gardens, breathing in the fresh air and tranquility.

afternoon
:

Spend the afternoon at a local spa, indulging in a massage or spa treatment designed to relax and revitalize. Enjoy the spa's amenities, such as saunas or tranquil relaxation areas, allowing yourself to unwind completely. After your treatment, savor a healthy lunch at the spa's café, focusing on fresh and wholesome ingredients.

evening
:

As the day winds down, participate in a guided meditation session that encourages reflection and inner peace. Enjoy a wholesome dinner at a farm-to-table restaurant, celebrating the flavors of the season. Conclude your wellness retreat with a peaceful evening walk, reflecting on your day of relaxation and self-care.

Discover Westchester

Read more in our Westchester 2025 Travel Guide.

Westchester Travel Guide