The Crooked Lake That Started It All

Keuka Lake is shaped like a letter Y, with two northern branches splitting at a narrow point called the Bluff. It’s the only Finger Lake that drains into another (its outlet flows north to Seneca Lake through Penn Yan), and its steep hillsides have been growing grapes since the 1860s — making this the birthplace of the Finger Lakes wine industry. The lake is smaller and quieter than Seneca or Cayuga, which is precisely the point. There’s no Interstate access, no chain-hotel strip. The towns at each end — Hammondsport to the south, Penn Yan to the north — run at a pace that rewards slowing down.

This itinerary starts in Hammondsport, loops up the east branch to Penn Yan, and finishes on the west shore for sunset. Total weekend driving: about 60 miles.

Day 1: Hammondsport

Morning: The Village and Depot Park

Hammondsport is a compact village of about 700 people at the southern tip of Keuka Lake. Start your morning with a walk around Depot Park, the grassy square at the foot of the lake where Pulteney Street meets the water. In summer, the park has a public beach (Champlin Beach) with a roped-off swimming area — one of the few free lake-access beaches in the Finger Lakes. The village square is a two-block loop: a handful of shops, a couple of cafes, and the kind of quiet that city visitors find disorienting in the best way.

Grab coffee and breakfast at the Village Tavern Restaurant and Inn on the square, or pick up pastries at one of the bakeries along Pulteney Street.

Mid-Morning: Dr. Konstantin Frank Winery

Drive five minutes north along the west side of the lake to Dr. Konstantin Frank Winery. Frank, a Ukrainian-born viticulturist, proved in the 1950s and ’60s that European Vitis vinifera grapes — Riesling, Gewurztraminer, Pinot Noir — could survive Finger Lakes winters. That breakthrough transformed the entire region from a producer of sweet Concord-grape wines into a serious viticultural area. The winery is still family-owned, now in its fourth generation.

The tasting room sits on a hill overlooking the lake with a commanding view of the Keuka bluffs. Their Rieslings (both dry and off-dry) and Rkatsiteli (a Georgian grape variety that Frank championed) are worth seeking out. Tastings are available without reservation during regular hours. Budget 30 to 45 minutes.

Late Morning: Heron Hill Winery

Continue north on the west shore for about 10 minutes to Heron Hill Winery. The tasting room here is built into the hillside with a wall of windows facing the lake — the view is one of the most dramatic on any Finger Lakes wine trail. Heron Hill’s Eclipse series represents their best vineyard selections, and the tasting staff is knowledgeable without being pretentious. Dogs are welcome on the deck. If the weather is good, bring your glass outside and take your time.

Afternoon: Glenn H. Curtiss Museum

Return to Hammondsport and spend the early afternoon at the Glenn H. Curtiss Museum on Route 54 at the southern edge of the village. Glenn Curtiss was a Hammondsport native who became one of the founding figures of American aviation — a rival and contemporary of the Wright Brothers. The museum houses restored early aircraft, vintage motorcycles (Curtiss started as a motorcycle racer and speed-record holder), and exhibits on early flight and the region’s aviation history. It’s engaging even if you’re not an aviation enthusiast: the craftsmanship of these early machines is remarkable. Admission is reasonable, and the museum is manageable in about 90 minutes.

The museum also covers Hammondsport’s role in early winemaking and the local boat-building tradition — giving you a broader picture of how this small village punched well above its weight in American history.

Dinner in Hammondsport

For dinner, stay in the village. The Park Inn, right on the square, serves American fare with a rotating seasonal menu — steaks, fresh fish, and pastas that lean on local ingredients. It’s the reliable neighborhood restaurant every small town wishes it had. Reservations are a good idea on Friday and Saturday nights.

Alternatively, Timber Stone Grill at the Pleasant Valley Inn, a few minutes south of the village on Route 54, offers a more upscale menu with Finger Lakes wines by the glass in a renovated historic building.

Day 2: The East Branch and Penn Yan

Morning: Keuka Outlet Trail

Start the day with a hike on the Keuka Outlet Trail, a 7.5-mile path that follows an old railroad bed along the Keuka Lake Outlet — the stream connecting Keuka Lake to Seneca Lake. The trail runs between Penn Yan and the hamlet of Dresden, and it’s mostly flat and well-maintained, making it suitable for all fitness levels. The route passes old mill ruins, cascading waterfalls, and dense forest. You don’t need to do the full out-and-back; a 3-mile stretch from the Penn Yan trailhead gives you the best waterfalls and ruins before turning back.

The Penn Yan trailhead has a small parking lot on Outlet Road. Get there by 8:30 on summer weekends to secure a spot.

Late Morning: Climbing Bines Hop Farm

From the trail, drive 10 minutes east of Penn Yan to Climbing Bines Hop Farm and Craft Ale Company. This is a working hop farm with a taproom — one of New York’s farm breweries that grows its own ingredients on-site. In summer, you can see the bines (the correct term — hops grow on bines, not vines) climbing their trellises in the fields behind the brewery. The beers are fresh, hop-forward, and distinctly local. The taproom has a relaxed, agricultural feel: picnic tables, a view of the hop yards, and often a food truck parked outside. Check their social media for taproom hours, which can be seasonal.

Lunch in Penn Yan

Head into downtown Penn Yan for lunch. The village sits at the northern tip of Keuka Lake’s east branch and has a walkable Main Street with a few solid options. Amity Coffee serves sandwiches and baked goods in a bright storefront. For something more substantial, Seneca Farms is a local institution for burgers, ice cream, and no-frills roadside dining — the kind of place where the line out the door on a July afternoon tells you everything. Penn Yan is also the home of Birkett Mills, one of the world’s largest buckwheat producers — look for buckwheat pancake mix at local shops as a take-home souvenir.

Afternoon: Steuben Brewing Company

After lunch, drive 20 minutes south to Steuben Brewing Company in Hammondsport. Another farm brewery, Steuben grows hops and grains on its property and produces a rotating selection of ales and lagers. The taproom occupies a renovated barn with an outdoor seating area. It’s a good spot to settle in for an hour with a flight and a conversation. Like many farm breweries, hours can vary by season — confirm before you go.

Sunset: The West Shore

For the final act of the weekend, drive the west side of Keuka Lake in the late afternoon. The road (Route 54A and connecting county roads) traces the shoreline with the sun lowering over the western hills behind you, lighting up the east-facing bluffs across the water. Pull off at one of the informal lakeside turnouts between Branchport and Hammondsport for the sunset. The Y-shape of the lake means the light plays differently here than on any other Finger Lake — the water catches color in three directions.

Where to Stay

• The Park Inn — Right on the Hammondsport village square, with simple rooms above the restaurant. Walking distance to everything in town.
• Black Sheep Inn & Spa — A boutique property just outside Hammondsport with a more upscale feel, lake-view rooms, and an on-site spa.
• Vacation rentals — Several lakefront cottages and houses are available on the west and east branches through VRBO and Airbnb. Booking early is critical for summer and fall weekends.

Trip Planning Notes

• Getting there: Hammondsport is roughly 90 minutes from Rochester, 4.5 hours from New York City, and 3.5 hours from Philadelphia. The nearest commercial airport is in Elmira (30 minutes south), with connections through Allegiant and Delta.
• Best time to visit: June through October. September is harvest season for both grapes and hops — the farm breweries are at their most active.
• Cell service: Spotty along rural stretches of the lake, especially the east branch. Download maps and directions before you leave Wi-Fi.
• Designated driver: Between wineries and breweries, this itinerary involves multiple tasting stops. Plan accordingly — split pours, use a designated driver, or hire a local tour service.