Woodstock

Day Trips

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

day 1
Explore Woodstock Nature
morning
:

Start your day with a refreshing hike at Overlook Mountain. Breathe in the fresh air and enjoy the incredible views of the Catskills.

afternoon
:

Visit the Woodstock Farmers Market to sample local produce and artisan goods. Grab a picnic lunch to enjoy in the scenic area.

evening
:

Enjoy dinner at a cozy local restaurant with live music. Stroll through the town and take in the vibrant local art scene.

day 2
Arts and Culture Day
morning
:

Spend the morning at the Woodstock Museum, discovering the town's rich artistic history. Check out rotating exhibits featuring local artists.

afternoon
:

Take a workshop at a local art studio, like painting or pottery. Create your own masterpiece to take home.

evening
:

Dine at a farm-to-table restaurant that highlights local ingredients. After dinner, catch a show at the Woodstock Playhouse for a taste of local theatre.

day 3
Relaxation Retreat
morning
:

Begin with a yoga session at a nearby studio, focusing on mindfulness and relaxation. Enjoy breakfast at a cafรฉ specializing in healthy options.

afternoon
:

Visit a local spa for a well-deserved massage or facial. Take time to unwind and rejuvenate.

evening
:

Have a peaceful dinner at a quiet spot with outdoor seating. Spend your evening reading or journaling in a tranquil environment.

day 4
Active Adventure
morning
:

Rent a bike and explore the scenic trails around Woodstock. Enjoy the beautiful landscapes and fresh air.

afternoon
:

Stop for lunch at a local deli, then head out for more cycling or try rock climbing at a nearby gym. Embrace the thrill and challenge.

evening
:

Relax with a casual dinner at a pub. Share stories of your adventures with fellow travelers and locals.

day 5
Music and Vibes
morning
:

Start the day with a visit to the Woodstock Music Shop to browse classic records. Learn about the town's music history.

afternoon
:

Attend a local music workshop or jam session to practice your skills. Immerse yourself in the creative atmosphere.

evening
:

Catch a live performance at a nearby venue, experiencing the essence of Woodstock's music scene. Enjoy late-night conversations with fellow music lovers.

day 6
Nature and Wildlife
morning
:

Visit the Woodstock Wildlife Sanctuary to learn about local flora and fauna. Take a guided tour or enjoy birdwatching.

afternoon
:

Pack a lunch and hike the trails at the sanctuary. Don't forget your camera for beautiful wildlife shots.

evening
:

Head into town for dinner and try a restaurant well-known for their local game dishes. End your day stargazing in a quiet spot outside town.

day 7
Day Outdoors
morning
:

Begin with a morning walk along the scenic Sawkill Creek. Enjoy the tranquility and sounds of nature.

afternoon
:

Explore the local trails for an invigorating hike. Have a packed lunch at one of the picturesque spots along the way.

evening
:

Have a hearty dinner at a communal dining restaurant. Reflect on your day's adventures over a cozy campfire if available.

day 8
Historical Exploration
morning
:

Visit the historic site of the original Woodstock festival. Learn about its significance in music history.

afternoon
:

Take a guided tour of a local historic home or site to dive deeper into Woodstock's past. Enjoy a light lunch at a local cafรฉ.

evening
:

Join a storytelling session or lecture on the history of the area. Wrap up your day with a light dinner reflecting on what you've learned.

day 9
Autumn Leaves
morning
:

Enjoy a leisurely walk in the woods to witness the stunning fall foliage. Grab a warm beverage from a local cafรฉ afterward.

afternoon
:

Visit nearby orchards for apple picking if in season. Perfect for making memories and delicious treats.

evening
:

Find a spot to enjoy dinner with charming autumn decor. Finish with a warm dessert, embracing the cozy autumn atmosphere.

Discover Woodstock

Read more in our Woodstock 2024 Travel Guide.

Woodstock Travel Guide