Olean

Day Trips

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

day 1
Arrival in Olean
morning
:

Arrive in Olean and settle into your accommodation. Enjoy a leisurely breakfast at a local café while enjoying the picturesque views of the countryside. Take a stroll around the quaint downtown area to take in the local shops and welcoming atmosphere.

afternoon
:

Visit the Olean Historical Museum to learn about the rich history of the region. Afterwards, relax at the nearby Lincoln Park, where you can take a leisurely walk or have a picnic. Don't forget to capture some photos of the park's beautiful landscaping.

evening
:

Dine at a local restaurant known for its farm-to-table offerings. After dinner, enjoy a quiet evening walk along the riverbank, where you can admire the sunset over the Allegheny River. You might also want to indulge in some ice cream at a local parlor to end your day on a sweet note.

day 2
Exploring Nature
morning
:

Start your day with a hike at the nearby Allegheny State Park, where you can enjoy the peaceful sounds of nature. Pack a light breakfast and make it an outdoor affair, surrounded by stunning foliage. Keep an eye out for local wildlife and beautiful vistas along the trails.

afternoon
:

After hiking, take a scenic drive through the park and stop for lunch at one of the many scenic overlooks. You might consider renting a kayak to paddle on the Allegheny Reservoir for a mix of excitement and relaxation on the water. Experience the beauty of the area from a different perspective while soaking up the sun.

evening
:

As dusk approaches, head back to Olean for dinner at a cozy restaurant showcasing regional cuisine. Attend a local theater performance or live music event to immerse yourself in the local arts scene. Reflect on the day's adventures over a nightcap at a bar downtown.

day 3
Cultural Immersion
morning
:

Visit the Regina A. Quick Center for the Arts on the campus of St. Bonaventure University. Start with an enriching experience by viewing the remarkable artwork and installations. Grab a coffee at the campus café while enjoying the academic ambiance.

afternoon
:

Explore the nearby sightseeing opportunities, including the historic downtown Olean district with its charming architecture and local boutiques. You can also visit the Olean Food Pantry, where volunteering can offer you a deeper connection with the community. Enjoy lunch in one of the downtown diners, known for their homemade dishes.

evening
:

Spend your evening sampling some local wines at a nearby vineyard or winery. Enjoy a unique dining experience with a wine pairing dinner, where you can learn about the local wine-making process. Wind down with a stroll through the arts district, appreciating the creative spirit that fills the evening air.

day 4
Adventure Day
morning
:

Kick off your day with an early breakfast before heading to the popular Olean Recreation Department for some morning activities. Try your hand at rock climbing or take a fitness class to energize your day. The community center offers plenty of options for active enthusiasts.

afternoon
:

Plan an adventurous afternoon at the Olean Bowling Center, where you can enjoy some friendly competition with friends or family. After a few fun rounds, grab lunch at the on-site diner, famously known for its comforting and filling meals. Consider visiting local antique shops after lunch for a unique shopping experience.

evening
:

Enjoy a fun-filled evening at a local arcade or bowling alley, surrounded by laughter and games. Celebrate your day with dinner at a family-friendly establishment, followed by a dessert treat from a local bakery. Capture the memories with a group photo before heading back for a cozy night.

day 5
Visit to Local Attractions
morning
:

Dedicate your morning to discovering the beauty of the Rock City Park, famous for its stunning rock formations and scenic views. Bring along a camera to capture the breathtaking landscapes. After a busy morning of exploration, visit a nearby café for a well-deserved brunch.

afternoon
:

On the return to Olean, stop by the Cutco Kitchen store for a fun glimpse into local manufacturing, and if you're lucky, catch a live demonstration. Enjoy lunch at a local pizzeria, known for its unique toppings and delicious flavors. Afterward, go on a shopping spree in Olean's independent shops for some unique souvenirs.

evening
:

Enjoy a delicious dinner at a waterfront restaurant, soaking in the beautiful sunset views. Consider spending the evening at a local urban lounge or bar enjoying live music. Return to your accommodation filled with joy and excitement from a day well spent.

day 6
Day of Relaxation
morning
:

Relax with a late breakfast at one of Olean's charming brunch spots, where you can savor homemade pastries and fresh coffee. Spend your morning at your leisure, enjoying some quiet time in your accommodation or exploring local markets. Take this opportunity to write in your journal or plan your next adventures.

afternoon
:

Indulge in a spa treatment at a local wellness center, where you can unwind with a massage or facial after a fun-filled week. Following your pampering session, grab a light lunch and head over to one of the parks for a tranquil afternoon in nature. Take a gentle walk or simply sit and read a book amidst the beautiful scenery.

evening
:

As your final evening in Olean approaches, enjoy an elegant dinner at an upscale restaurant featuring seasonal ingredients. Look for a spot that boasts a view to create a memorable dining experience. Cap off your trip with an evening stroll through the serene streets, reflecting on the wonderful memories you've made.

day 7
Departure from Olean
morning
:

After packing and checking out of your accommodation, enjoy a final breakfast at a favorite café. Take a moment to reflect on your visit and capture any last-minute photos in Olean. Check your travel arrangements and prepare for your departure.

afternoon
:

Before leaving town, venture to a local gift shop to pick up some final souvenirs to remember your stay. Enjoy lunch at a nearby diner, savoring the tastes of Olean one last time. Use the afternoon to leisurely explore any spots you may have missed, making the most of your remaining time.

evening
:

As you wrap up your visit, embark on your journey home, taking with you the memories of the beauty and warmth of Olean. Share stories and photos with friends and family about your adventures. Reflect on the experiences you had and the connections you built, with the promise to return someday.

Discover Olean

Read more in our Olean 2025 Travel Guide.

Olean Travel Guide