How to Plan the Perfect Long Weekend in New York’s Finger Lakes

A few weeks ago, The Shire went on our annual family vacation. My parents are huge history buffs, so growing up we spent every summer in Williamsburg, VA, which has practically become a home-away-from-home to me. Yet as much as I love Williamsburg, now that I’m an adult and typically the person planning our trips (hazard of travel blogging!), we often mix it up. Last year we went to Boston and loved it, and it’s been relatively easy to convince The Shire to explore some new places ever since.

Clearly The Shire enjoyed The Finger Lakes!

We have pretty diverse interests, and so it’s often challenging to find a place that’s a good fit for all of us. This year we decided we wanted something more relaxing than our usual breakneck pace; something northern, so that we wouldn’t be miserably hot the entire time; and something that had the proper combination of good food and wine, nature, and (of course) history.

I’ve wanted to visit The Finger Lakes for a long time, and they seemed to fit the bill!

Since I did a lot of research to find all the good spots and things to do, and crowd-sourced some suggestions from my very helpful friends, I wanted to share our itinerary in case anyone else is searching for a great place to spend a long weekend.

Where to Stay

If possible, I would encourage you to rent a lakefront cabin (Airbnb, Finger Lakes Premiere Properties, and Homeaway are great resources). Since we threw this trip together just a couple weeks in advance, we wound up at a hotel.

We stayed at the Best Western Plus Vineyard Inn & Suites in Penn Yan, just off of Keuka Lake. It was one of my better hotel stays in all my years of traveling, and I would highly recommend it! Our rooms were huge, the hotel was very clean, the free breakfast was decent, the location was incredibly convenient, and most of all, the staff was just unbelievably friendly and cheerful. Maybe it’s all the wine in the region!

Keuka Lake

Another great alternative would have been the Hampton Inn Penn Yan, since it is lakefront.

We didn’t end up spending much time in Penn Yan (it’s tiny!) but we heard good things about La Cocina, The Waterfront, and Pleasant Valley Inn (over in Hammondsport), though we never got to dine at any of them.

Day 1

On our first full day in The Finger Lakes, we headed directly into Watkins Glen, at the bottom of Seneca Lake. Our top priority for the trip was to hike Watkins Glen State Park, one of the most widely acclaimed parks in the country. Watkins Glen is famous for its 2-mile Gorge Trail, which allows you to see 19 breathtaking waterfalls.


Some tips for hiking Watkins Glen: come early on a weekday, if possible, because the Gorge Trail gets really crowded, especially in the summer. There are other trails in the park as well, but the Gorge is the one that everyone is there to see. There are no restrooms along the trail, but there’s a decent welcome center where you can make a pit stop before starting your hike. They also sell snacks and gifts, etc.

Parking at Watkins Glen costs $8, but the trail is free. We actually took the shuttle ($5 per person) to the top of the Gorge Trail (the North Entrance) rather than starting from the Main Entrance, and hiked our way back down to the car. This was great because it allowed us to just hike the trail once, rather than having to go all the way up and all the way back down. It also allowed us to take the 800+ steps that comprise the trail downhill instead of uphill. We’re all in decent shape, but my very athletic dad has had 7 knee surgeries, and we didn’t want him to be uncomfortable the rest of the trip. Even if you’re an Olympian, I’d still recommend only doing the trail one way.

The park itself is open sunup to sundown, and while you can hike the trail in an hour, I would suggest allotting two for ample photo stops. You’ll just want to soak in as much of the extraordinary views as you can!

Speaking of soaking, be sure to wear clothes that you don’t mind getting wet. There are two waterfalls that you walk underneath, but most significantly – your shoes will be damp by the end. We wore sneakers (you need something with decent grip, as the steps are slippery in many spots) and definitely needed to change our shoes afterwards!


After hiking, we hit the Seneca Lake Wine Trail from the top of the lake (just below Geneva) to the bottom, near Watkins Glen.

It’s worth noting that while we were very lucky because my dad, who is not a big wine drinker, willingly volunteered to be our Designated Driver, there are plenty of local services that can safely chauffeur your group around if needed.

There are hundreds of wineries in the Finger Lakes, but we concentrated on the western side of Seneca Lake simply for convenience. The region is known for its Dry Rieslings, and I would definitely encourage you to try them, even if you’re typically a dry red drinker, like me. We also wound up trying lots of chardonnay, another wine I don’t really love. However, The Finger Lakes version of chardonnay is aged in steel barrels rather than the typical oak barrels, and consequently has a fresher, crisp taste, rather than the buttery flavor you get from a California chardonnay. I found that I preferred unoaked chardonnay, and was pleasantly surprised by the wine. If you still want your dry reds, try some Lemberger, which is another area staple.

Fox Run Vineyards

Most wineries offer a tasting of five different wines for $5, and some even have full cafés or restaurants where you can order a meal. We started out at Fox Run Vineyards, where we had an incredible cheeseboard (they have GF options!), among some other snacks. Fox Run had great food, good wine, and a famous Garlic Festival that happened to coincide with our trip, and I would definitely go back!


Next we stopped at Miles Wine Cellars, which had some of my least favorite wine of the trip, but incredible views of the lake. Miles is also home to an inn, and is absolutely gorgeous. A tiny tasting room, but worth a visit just to scope out the scenery!

Miles Wine Cellars

From there we swung by Magnus Ridge Winery, which looks like it’s been ripped out of the French countryside and plunked down in New York. Again, not my favorite wine, but a beautiful courtyard complete with water features.

Magnus Ridge Winery

Our fourth stop was Herman J. Wiemer, and this was by far the best wine of the trip. Our tasting guide was incredibly knowledgeable (and also gave us some extra pours!), and everything from the sweeter whites to the spicier reds was excellent. We bought a lot of wine from this vineyard and I’m looking forward to enjoying it at home, especially the HJW Vineyard Riesling!

Herman J. Wiemer, my favorite winery we visited.


Finally, we rounded out our tastings at Glenora Wine Cellars, where I found a sparkling wine that I really enjoyed. Glenora has a beautiful view of the lake, too!

We headed back to Penn Yan for dinner, and ate at Silverbird Woodfired & Gastropub. I had pan-seared bacon-wrapped scallops with brussels sprouts and carrot and parsnip fries, and the meal was amazing!!!

Day 2

On Friday we headed to Corning, to visit the Corning Museum of Glass, which everyone told us was a “must see.” They were right – the museum was incredible, showcasing everything from glassblown modern art pieces, to a fascinating science exhibit on the history of glass, to live demos from artisans that will blow your mind (pun intended). The museum is $19.50 per adult (there are AAA and other discounts), and worth every penny. They recommend roughly 2 hours to tour the museum, but we spent 4. I would highly encourage you watch one of the glass demos – it was my favorite part of the museum.



Each one of these butterflies is cut from solar panels, and powers the chandelier.
A lynx made entirely of glass!


If you want to grab lunch afterwards, the nearby Old World Café & Ice Cream is a local favorite, but we headed back to the Seneca Lake Wine Trail, stopping at Shtayburne Farm to pick up some cheeses and snacks. (The Finger Lakes also have a Cheese Trail. Yes, you read that properly!) We spent the afternoon at Lakewood Vineyards and Barnstormer Winery (conveniently located right next to each other) and really enjoyed both. Barnstormer had a solid Sangiovese rosé if you enjoy rosés as much as I do!

Seneca Lake

We wound up in Watkins Glen at Seneca Harbor Station for dinner that night on the water, and it didn’t disappoint. I would highly recommend rounding out your meal with The Harbor Raspberry Bongo: cream puffs piled with mascarpone and cream cheese, topped with fresh raspberries, chocolate sauce, and Chambord. Other Watkins Glen dining suggestions include: Nickel’s Pit BBQ, Rooster Fish Brewing, Jerlando’s Ristorante and Graft Wine & Cider Bar.


Day 3

We kicked off our final day in The Finger Lakes with Captain Bill’s Seneca Lake Cruises, and it was awesome! Our tour guide was incredibly knowledgeable and we learned all sorts of cool things about the region. The tour was $20 per person, and takes you on a 1-hour cruise around Seneca Lake. We saw Native American cliff painting, waterfalls, and all sorts of beautiful scenery.


Next, we headed into Geneva to visit Rose Hill Mansion, which was (quite surprisingly for a family of history buffs!) our least favorite stop of the trip. It’s a gorgeous 1800s Greek Revival house that overlooks the water, but the tour was sort of dry. It only cost $10 and was right across from Ventosa Vineyards, a massive Tuscany-inspired winery that has a gorgeous view of the lake. We then swung by Belhurst Castle & Winery (which also has a very nice but affordable inn and a couple of restaurants which looked good) and spent a few hours just relaxing on their lakefront patio.

Rose Hill Mansion


Dinner that night was in Geneva, at Halsey’s, (which had excellent GF artisan pizzas), and then we tucked into bed so that we could hit the road bright and early. Other Geneva restaurants to check out: Ports Café or Beef & Brew.

Belhurst Castle & Winery


Hopefully that overview helps you plan a nice long weekend in The Finger Lakes region! I would love to go back some day and would definitely recommend it as a great place to eat, drink, relax, and enjoy nature.

Penny for your thoughts?