Things to Do in Olean, New York

One of Olean’s most distinctive attractions is Woodland in the City, a public art trail featuring nearly 30 life-sized fiberglass squirrels displayed throughout downtown and local neighborhoods. Each squirrel is uniquely designed with its own theme, celebrating Olean’s history, businesses, and community spirit. Visitors can turn exploring the city into a scavenger hunt while discovering local shops, restaurants, parks, and public spaces along the way.

More than a public art installation, Woodland in the City supports the Historical & Preservation Society of Olean and reflects the community’s commitment to preserving local history while creating memorable experiences for residents and visitors alike. Whether you’re strolling downtown or spending the weekend exploring, the squirrel trail offers a fun and uniquely Olean way to experience the city.

Learn More:

• Interactive Squirrel Map Here.

Photo credit: City of Olean.

Just 15 minutes from downtown Olean, Allegany State Park is New York’s largest state park, offering more than 65,000 acres of forests, lakes, and trails. Visitors can hike, bike, kayak, fish, camp, and enjoy year-round recreation, including vibrant fall foliage and cross-country skiing in winter.

Learn more: https://visitanf.com/allegany-state-park-new-york/

Photo credit: Allegany State Park, New York State Parks.

Living in Olean means you’re surrounded by some of Western New York and northwestern Pennsylvania’s most memorable destinations. Within an hour, you can spend the day hiking through the 65,000-acre Allegany State Park, skiing or mountain biking at Holiday Valley in Ellicottville, walking the Kinzua Sky Walk overlooking one of Pennsylvania’s most iconic overlooks, or exploring the Seneca Nation’s history and culture in nearby Salamanca. The region also offers scenic drives, wineries, festivals, lakes, and year-round outdoor recreation, making it easy to plan a different weekend adventure every season. Whether you’re looking for outdoor adventure, small-town shopping, or family-friendly attractions, Olean is an ideal home base for exploring the Southern Tier and Allegheny region.

Helpful links:

• Learn more about Allegany State Park.
• Explore Holiday Valley Resort.
• Visit Ellicottvile.
• Discover Kinzua Bridge State Park.
• Learn about Salamanca and the Seneca Nation.

Photo credit: Allegany State Park, Holiday Valley Resort, Kinzua Bridge State Park, the Seneca-Iroquois National Museum, and Enchanted Mountains of Cattaraugus County.

Downtown Olean is the heart of the community, where historic architecture, locally owned businesses, and neighborhood traditions create a welcoming atmosphere year-round. Centered along North Union Street, downtown offers an easy-to-walk district filled with restaurants, specialty shops, boutiques, and gathering spaces that showcase the city’s character.

Dining is a local tradition. Beef ’N Barrel has been a longtime favorite for steaks, seafood, and classic American fare, while Angee’s Restaurant is known for its homemade Italian dishes and friendly, family-owned atmosphere. For shopping, Christie’s Boutique offers clothing, gifts, and home décor from independent brands, making it a favorite stop for both residents and visitors.

Beyond shopping and dining, downtown hosts community events throughout the year, including the Olean Farmers Market, Tunes on Tuesday summer concerts, holiday celebrations, and seasonal festivals that bring neighbors together. Whether you’re enjoying dinner with friends, browsing local shops, or spending an afternoon downtown, Olean offers the kind of locally owned businesses and community connections that make it easy to feel at home.

Explore Downtown Olean:

• 🍽️ Beef ’N Barrel Restaurant – View the menu and hours.
• 🍝 Angee’s Restaurant – Explore the menu and plan a visit.
• 🛍️ Christie’s Boutique – Browse local gifts, clothing, and home décor.
• 🎉 Greater Olean Area Chamber of Commerce – See upcoming events and festivals.

Photo credit: Beef ‘N Barrel, Angee’s Restaurant, Christie’s Boutique, and the Greater Olean Area Chamber of Commerce.

Surrounded by the forests, rivers, and rolling hills of New York’s Southern Tier, Olean offers outdoor recreation in every season. Just minutes from the city, Allegany State Park spans more than 65,000 acres, making it New York’s largest state park and a destination for hiking, mountain biking, camping, kayaking, fishing, wildlife viewing, and cross-country skiing. The nearby Allegheny River provides additional opportunities for paddling and fishing, while scenic drives and nearby trails showcase some of the region’s most vibrant fall foliage. Whether you’re looking for a weekend adventure or a quick evening on the trail, outdoor recreation is part of everyday life in Olean.

Plan Your Adventures:

• 🥾 Explore Allegany State Park
• 🚣 Discover outdoor activities in the Enchanted Mountains
• 🚴 Find hiking and biking trails near Olean
• 🎣 Learn about the Allegheny River

Photo credit: Enchanted Mountains of Cattaraugus County, New York State Parks, and the Allegheny River Valley Trail Association.