Located in the heart of New York’s beautiful Finger Lakes region, the community of Penn Yan exudes small-town charm and picturesque scenery. In the summer, head straight for the cool waters of Keuka Lake. During the fall, the tree-covered hillsides around town turn into brilliant oranges and reds. When winter comes around, it brings peaceful snow sports throughout the local meadows. While you’re booking a stay at the perfect Penn Yan vacation rental, you’ll be situated near these popular local attractions.

1. Paddle Keuka Lake

Get a spectacular view of the forested hills around Penn Yan with a paddle trip on Keuka Lake, one of the area’s favorite attractions. Rent canoes, kayaks, or stand-up paddle boards from Moran Marine, which offers a convenient onsite launch spot. Watch birds in the marshes at the north end of the lake. For the calmest waters, stay within 200 feet of the shore; according to local regulations, speedboats must slow to 5 mph in that area.

2. Explore the L. Caroline Underwood Museum

Immerse yourself in the women’s suffrage movement at the L. Caroline Underwood Museum. As you walk through the historic home, examine early 20th century dresses worn by suffragettes, and check out actual petition boards from suffrage parades in New York City. Outside, stop into the Scherer Carriage House to view a coachee carriage from the late 18th century, and discover the story of its owner, Jemima Wilkinson, and her pioneer followers in the Society of Universal Friends.

3. Bike the Keuka Lake Outlet Trail

Pick up a mountain bike from Shoreline Rentals and hop on the Keuka Outlet Trail, a 7-mile route that follows the historic Crooked Lake Canal. As you pedal through the tree-lined ravine, look out for the locks that once allowed ships to travel between Seneca Lake and Keuka Lake. With its gentle slopes and ample stopping-off points, the round trip makes a fun afternoon for kids and adults.

4. Golf at Lakeside Country Club

High on the hills above Keuka Lake, the Lakeside Country Club offers panoramic views from its par 72 golf course. Work on your chipping in the practice area, or head straight for the long, manicured fairways to take in lake views as you play a leisurely 18 holes. Well-maintained golf carts make it easy to travel the rolling course, and the onsite pro shop offers lessons.

5. Drive the Keuka Lake Wine Trail

From its location in the heart of the Finger Lakes wine country, Penn Yan offers easy access to the Keuka Lake Wine Trail. Sip locally made cabernet sauvignon with a view of the lake from the patio at Keuka Spring Vineyards, and head over to Vineyard View Winery for a wine tasting or a dry flight in the rustic tasting room. Other local stops include Point of the Bluff Vineyards and Ravines Wine Cellars.

Find the perfect Penn Yan vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

6. Visit the Oliver House Museum

Step back in time to the 19th century at the Oliver House Museum, which sits in a grand Italianate home in Penn Yan. As you explore the 18 rooms, check out Victorian furnishings and look out for the fascinating wood-fired cooking stove in the kitchen. Knowledgeable docents can offer guided tours, and families with kids are always welcome.

7. Take a Pontoon Cruise

Explore the legendary Y-shaped Keuka Lake in style aboard a pontoon cruise with Keuka Watersports. Board the boat in Hammondsport, and sit back as you glide past historic farms and palatial waterfront homes. If you’re visiting with a group, charter a private cruise with an experienced local captain.

8. Try Water Skiing

See the shoreline at high speeds with a water skiing trip down Lake Keuka. The long, narrow lake enables marathon ski runs with few to no turns, making it a great option for beginners and speed demons. Head over to Basin Park Marina in Branchport to rent a ski boat; the company also offers skis, wakeboards, and tubes.

9. Fish Keuka Lake

Land an enormous bass on Keuka Lake, which is known for its huge fish. For kids and new anglers, the summer is a great time to fish; smallmouth bass are plentiful and responsive to live bait. Fish from the shore at the Penn Yan Boat Launch or Indian Pines Park. If you’re interested in secret fishing spots, book a guided day trip with Bobber’s Fishing Charters.

10. Cross-Country Ski at Keuka Lake State Park

When snow blankets the Finger Lakes region, pack up your cross-country skis and head to Keuka Lake State Park. To the east of the campground, a series of winding trails offer fun, challenging terrain. Hop on the Green Trail to access the remote Orange Trail, where you can loop through the trees in absolute silence. The winds off the lake can be cold, so stop at Keuka Lake Coffee Roasters on your way to the park to fill a thermos with hot coffee.

11. Hike the Townsend-Grady Wildlife Preserve

Get away from it all with a hike through the Townsend-Grady Wildlife Preserve. Start your visit in the onsite Finger Lakes Museum and Aquarium, where you can see photos of the fox, beaver, and local birds that make their home in the wetlands. Then, follow the boardwalk as it meanders through 16 acres of wetlands, stopping to read the interpretive signs and watch kayakers paddle down Sugar Creek.

12. Try the Finger Lakes Beer Trail

Experience the booming local beer scene on the Finger Lakes Beer Trail. Start at Lyon Smith Brewing, where you can sample unique beers that are difficult to find outside of the United Kingdom. Then, head east to the Climbing Bines craft ale and hop farm to taste house-made beer, play frisbee golf, and see hops in all stages of growth.

13. Pick Fresh Fruit at Serendipity Blueberry Farm

Experience the booming Yates County agritourism culture at Serendipity Blueberry Farm. Each year, the fields burst with blueberries, and local families pick their fill under the sunshine. Let the kids play in the rows of trees while you fill containers with fruit to bring back to your vacation rental.

14. Visit the Rochester Folk Art Guild

Surround yourself with artisans at the Rochester Folk Art Guild, which sits 13 miles west of Penn Yan. Multiple times per year, this intentional community and craft center opens its studios and stores to the community. Wander through a historic barn, watch potters in action, and speak to woodworkers and weavers about their traditional processes.

15. Stop By the Birkett Mills

If you’re a fan of hearty buckwheat, the Birkett Mills is one of Penn Yan’s must-see destinations. See where buckwheat is processed and transformed into groats, flour, and more, and stock up on locally made items in the onsite gift shop.

Ready to go? Check out these amazing Penn Yan vacation rentals on Tripping.com.