Philipstown

Day Trips

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

day 1
Exploring Philipstown
morning
:

Start your day with a refreshing hike at Breakneck Ridge. Enjoy the beautiful views of the Hudson River and surrounding mountains.

afternoon
:

Visit the nearby Cold Spring village for lunch at a charming café. Spend some time exploring the local boutiques and art galleries.

evening
:

Wrap up your day with a scenic sunset view from the shores of the Hudson River. Enjoy dinner at a local restaurant with river views.

day 2
Nature and History
morning
:

Visit the Hudson Highlands Nature Museum and learn about the local ecology. Take a stroll on the trails to immerse yourself in nature.

afternoon
:

Explore the historic sites in Philipstown, including the Old Cadet Academy. Grab a bite at a local deli or picnic in one of the parks.

evening
:

Take part in a community event or concert if available. Savor some ice cream while walking around the town center.

day 3
Relaxing River Day
morning
:

Start with a leisurely breakfast at a riverside café. Then, rent a kayak and paddle on the Hudson River.

afternoon
:

Enjoy lunch at a waterfront eatery while soaking in the ambiance. Spend the afternoon fishing or relaxing by the water.

evening
:

Attend a sunset yoga session by the river. Enjoy a cozy dinner at home or at a local bistro.

day 4
Art and Culture
morning
:

Visit a local art gallery to appreciate works by Hudson Valley artists. Participate in a morning art workshop if available.

afternoon
:

Explore the Boscobel House and Gardens to admire historical architecture. Have lunch at the onsite café overlooking the gardens.

evening
:

Attend a local theater performance or music event. Dine at a restaurant that features live music.

day 5
Family Fun Day
morning
:

Head to the local park for a family picnic breakfast. Let the kids enjoy the playground and open spaces.

afternoon
:

Visit the local zoo or animal sanctuary to connect with wildlife. Enjoy a family-friendly lunch at a nearby pizzeria.

evening
:

End the day with a family movie night at home or in a local theater. Consider ordering takeout from a favorite family restaurant.

day 6
Historical Walkabout
morning
:

Start your day with a walking tour of Philipstown, highlighting its rich history. Visit the local historical society for insights.

afternoon
:

Have lunch at a historic inn or tavern to enhance the experience. Continue your exploration by checking out the local library.

evening
:

Enjoy a quiet evening strolling along the river with friends or family. Treat yourself to dinner at a classic American diner.

day 7
Outdoor Adventure
morning
:

Embark on a mountain biking adventure in the nearby state parks. Have coffee and pastries at a local shop before hitting the trails.

afternoon
:

After your biking session, relax by the river or explore more challenging trails. Grab a food truck lunch for a quick bite.

evening
:

Join fellow outdoor enthusiasts for a bonfire or camp night if available. Roast marshmallows and share stories under the stars.

day 8
Garden Serenity
morning
:

Begin your day with a visit to the nearby botanical gardens. Enjoy the peaceful surroundings and beautiful blooms.

afternoon
:

Have a light lunch at the garden café, surrounded by nature. Consider participating in a floral arrangement workshop.

evening
:

End your day with a sunset walk through the gardens. Dine at a tranquil restaurant that focuses on farm-to-table cuisine.

day 9
Culinary Exploration
morning
:

Join a local cooking class to learn about Hudson Valley cuisine. Start with a hearty breakfast of farm-fresh ingredients.

afternoon
:

Enjoy the lunch you prepare in class, paired with local wines. Visit local farms or markets to discover fresh ingredients.

evening
:

Finish with a food tasting tour of the neighborhood’s best eateries. Sample various cuisines and indulge in desserts.

day 10
Scenic Driving Tour
morning
:

Set off on a scenic drive along the Hudson River. Make stops at viewpoints to take photos of the stunning landscapes.

afternoon
:

Stop for lunch at a cozy riverside restaurant. Explore additional quaint towns along the way.

evening
:

Return to Philipstown and enjoy a relaxed dinner while reflecting on the day’s adventures. Consider a nightcap at a local bar.

Discover Philipstown

Read more in our Philipstown 2024 Travel Guide.

Philipstown Travel Guide