Peekskill

Day Trips

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

day 1
Explore Nature in Peekskill
morning
:

Start your day with a refreshing hike at the nearby Blue Mountain Reservation. Enjoy the scenic views and breathe in the fresh air while you explore the trails.

afternoon
:

Visit the Peekskill waterfront for a leisurely lunch by the river. After your meal, take a stroll along the pier and enjoy the picturesque surroundings.

evening
:

End your day with a dinner at a local restaurant featuring farm-to-table dishes. Consider catching a live music event at the Paramount Hudson Valley Theater.

day 2
Arts and Culture Day
morning
:

Visit the Hudson Valley Center for Contemporary Art to admire the exhibits. Take your time to engage with the unique art pieces on display.

afternoon
:

Explore the historic downtown area and pop into local galleries and boutiques. Grab lunch at a cozy café that showcases local art.

evening
:

Attend a theater performance or art show at one of the local venues. Finish the night with dessert at a charming bakery.

day 3
Adventure on Wheels
morning
:

Rent a bike and ride along the scenic Hudson River Greenway. The morning breeze and stunning views make it an energizing start.

afternoon
:

Stop for lunch at a riverside restaurant and then continue your bike ride towards Croton Point Park. Enjoy the natural beauty as you pedal along.

evening
:

Return the bikes and unwind with a picnic dinner at the Peekskill waterfront. Watch the sunset over the river while enjoying a relaxing meal.

day 4
Wine and Dine Experience
morning
:

Join a guided tour of local wineries for a morning of tastings. Learn about the winemaking process while enjoying the scenic vineyard views.

afternoon
:

Have a leisurely lunch at one of the winery restaurants that pair dishes with wines. Savor the flavors while soaking in the vineyard ambiance.

evening
:

Attend a wine and food pairing event for an elegant dining experience. Choose from various local venues that specialize in gourmet meals.

day 5
Lakeside Serenity
morning
:

Head to Lake Peekskill for some peaceful morning kayaking. Paddle along the tranquil waters and enjoy the beauty of your surroundings.

afternoon
:

Pack a picnic lunch to enjoy by the lakeshore. After your meal, take a relaxing walk around the lake's perimeter.

evening
:

Catch a beautiful sunset over the lake and enjoy a quiet evening. Consider wrapping it up with a warm drink at a nearby café.

day 6
Scenic Walks and Discovery
morning
:

Take a guided walking tour of Peekskill to learn about its rich history. Discover historical landmarks and hidden gems in the area.

afternoon
:

Enjoy lunch at a local diner that offers classic American fare. Post-lunch, visit the Peekskill Museum to dive deeper into the town’s history.

evening
:

Find a local pub for dinner and socialize with residents. Experience the community vibe and perhaps catch some live local music.

day 7
Shopping and Local Finds
morning
:

Explore the local farmers market and indulge in fresh produce and handmade goods. It's a great way to support local artisans.

afternoon
:

Visit unique shops and boutiques downtown for some local shopping. Enjoy lunch at a nearby café with farm-fresh ingredients.

evening
:

End the day with a casual dinner at a restaurant known for its eclectic menu. Consider trying something new and locally sourced.

day 8
Music and Entertainment
morning
:

Visit the Red Apple Rest, a storied roadside landmark, and enjoy a classic breakfast. Take your time exploring the history of this iconic spot.

afternoon
:

Spend your afternoon at a local music venue for an open mic event. Grab a light lunch and enjoy discovering new local talent.

evening
:

Attend a concert or performance at the Paramount Theater. Enjoy an evening filled with great music or comedy.

day 9
Outdoor Explorer's Delight
morning
:

Start your day with a hike at the nearby Croton Point Park. The trails offer beautiful views of the Hudson River and the surrounding nature.

afternoon
:

Pack a lunch and enjoy a scenic picnic at one of the park's designated areas. Spend time watching the local wildlife and soaking up the sun.

evening
:

As the sun sets, consider a guided night hike or star-gazing event. Wrap up the day by sharing stories around a fire pit.

day 10
Movie Night and More
morning
:

Spend a relaxed morning at a local coffee shop with your favorite book. Enjoy the cozy atmosphere and chat with locals.

afternoon
:

Catch a matinee showing at the local cinema for a fun movie experience. Pair it with lunch at a popular nearby eatery.

evening
:

Explore local dining options for dinner, perhaps finding a unique themed restaurant. Finish off the night with dessert and a stroll.

Discover Peekskill

Read more in our Peekskill 2024 Travel Guide.

Peekskill Travel Guide