The Best Small Town In The Finger Lakes For A 3-Day Weekend

On a map, Hammondsport looks like a pin at the end of Keuka Lake. In person, it feels like a Finger Lakes oasis designed to conserve your time. Keuka Lakeside Inn’s dock, Main Street cafés, and the Park Inn’s dining room sit close enough that a car becomes optional after check-in, even for a late-night scoop at Crooked Lake Ice Cream.

The same walkable layout is why Glenn Curtiss chose Hammondsport as a home base for early flight experiments; he could tinker, test, and return to town in minutes. That legacy lives on at the Curtiss Museum’s restoration shop, where volunteers still rebuild history by hand. A three-day weekend fits neatly here, with every stop close and unhurried.

Lakeside Living

Stay right on the lake at the Keuka Lakeside Inn, which is equipped with 17 rooms that are all loaded with modern amenities, including in-room climate control, flat screen television, coffee maker, and refrigerator. Keuka Lakeside Inn offers the best of both worlds in Hammondsport: it is located only a short walk from everything downtown has to offer, and has over 230 feet of lakefront, including an on-site boat launch and a gas-powered fire pit on the water’s edge.

Black Sheep Inn and Spa may only have six guest rooms, but they are all loaded with luxury, including private en-suites and either mountain or garden view, a two-course breakfast, and large, spacious common areas with books, games, and puzzles. On-site spa treatments are offered by the inn’s licensed therapists and include individual Swedish massages, hot stone massages, and deep tissue massages. There are also package options available when booking, such as the Romantic Getaway package and the Black Sheep Concierge Tour, which takes guests on tours to local wineries, breweries, or distilleries.

Walkable Downtown

The Restaurant at the Park Inn is a standout farm-to-table experience in Hammondsport, known for its seasonally focused menu that is centered around locally produced and sourced ingredients. A wide selection of drinks is available to pair with food items on the menu, including more than 200 wines from the Finger Lakes and international regions, traditional and craft beers, and both classic and signature house cocktails. Just off the village square, Crooked Lake Ice Cream Company adds a retro, family-friendly stop for breakfast, sandwiches, and sundaes, while Service Station FLX on Main Street serves small-batch coffee, quiche, and light lunches in a relaxed, bike-friendly café space.

The Aroma Coffee Art Gallery offers a unique blend of art gallery and coffee shop, making it a great place to enjoy breakfast or lunch—highlights of the menu include shakshuka—while viewing works of art on the wall which are also for sale. Just around the corner, Opera House Antiques offers a variety of antiques, collectibles, and vintage items, including furniture, jewelry, fishing items, glass, linens, period clothing, prints and paintings, and much more. The Cinnamon Stick on Mechanic Street leans into cozy gifts, gourmet treats, and home décor, and nearby Browsers of Hammondsport rounds out the downtown experience with two floors of locally inspired souvenirs, clothing, and lake-themed finds.

Aviation History

The Glenn H. Curtiss Museum pays homage to the local pioneer in aviation and mechanics, Glenn Curtiss. The museum features exhibits which showcase early aviation and regional history, a 75-seat theatre, a large open area that hosts special events, a museum store, and the Restoration Shop where visitors can observe volunteer craftsmen work on historic aircraft. The museum is located half a mile south of Hammondsport and is open year-round except for Easter, Thanksgiving, Christmas Eve, Christmas Day, and New Year's Day. Other than aircraft, the museum also houses collections of automobiles, motorcycles, and bicycles. For groups that visit the museum, both guided and self-guided tours can be scheduled by contacting the museum directly.

Exploring the Outdoors

Keuka Lake is the third largest of the Finger Lakes at 19.6 miles long, 1.9 miles wide, and 183 feet deep. It is a premier location for fishing, boating, and swimming, with other activities around the lake, including hiking and biking. There are multiple public boat launches around the lake, and several marinas where you can rent your own boat; landlocked salmon and several species of trout are routinely caught, and there are several beaches around the lake that are accessible from Hammondsport which allow for a place to relax in the sand, or swim in the water permitting there is a lifeguard on duty. Keuka Lake is best visited between May and October when the weather is more favorable for recreating in or around the lake.

Hammondsport’s central location makes it a great base camp for exploring places in the Finger Lakes region, like Watkins Glen State Park, which is about a 40-minute drive from town, making it a great trip on one of the days of your 3-day weekend. While the park is open year-round, it is best visited from mid-May to mid-October as the weather is warm and most activities are available, like the Watkins Glen State Park Gorge Trail, which is the most popular activity in the park and is not accessible in the winter months. The trail features 832 stone steps that descend 400 feet into the gorge, following Glen Creek, which creates 19 waterfalls along the path that range in height between three and 60 feet. During peak season, many picnic shelters and pavilions are available to rent.

Three Days in the Finger Lakes

Hammondsport is a great place to spend a 3-day weekend, as it allows you to spend your time in whichever way you want. The small town feeling makes it a great place to simply relax and escape from the hustle of city life, its nearby natural areas make it a great base camp for further exploring the Finger Lakes region, and its downtown is small enough to be explored on foot but still manages to include everything you need for some much-needed time away.

Similar Towns Nearby

Just up the shore, Penn Yan feels like Hammondsport’s slightly bigger cousin and makes an easy add-on or alternate weekend base. The village stretches along the north end of Keuka Lake, with a compact downtown of brick storefronts, cafés, and wine bars that still feel rooted in the farming countryside around it. The Keuka Outlet Trail begins right in town, following the old canal route toward Seneca Lake with waterfalls, wooded stretches, and traces of the mills that once powered the local economy. Lakeside parks and low-key waterfront restaurants make it simple to spend an unhurried afternoon or a full two-night stay.

A short drive away, Watkins Glen offers another small-town retreat that blends scenery and walkability. The village sits where its dramatic gorge meets Seneca Lake, so a weekend here naturally flows between hiking and harbor time. Mornings can be spent on the trails in Watkins Glen State Park, passing one waterfall after another along the stone-lined gorge, while afternoons shift to shops, tasting rooms, and casual eateries along Franklin Street. With a mix of inns, vacation rentals, and the lakeside Watkins Glen Harbor Hotel right at the waterfront, it’s easy to park the car and settle into a slow-paced Finger Lakes weekend.