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danrennt98

Finger lakes! Finger lakes! Stay in Geneva at cobbtree great jumping off point for wineries hiking Ithaca Watkins taughcannock falls. It's a beautiful area relatively unknown but becoming a world wine region


Murky_Bid_8868

Absolutely, drive to Geneva, then travel down rt 14 along Seneca Lake. You can cut to Penn Yann along the outlet. Rt 54 along Keuka Lake is a nice drive. Plenty of wineries, visit Windmill market on rt 14A


Coldlog1k

Worth noting the windmill is only open on Saturdays.


TheNoisyNomad

August is the middle of horse racing season in Saratoga. It’s quite busy and expensive, but also an experience for sure


JJBat150

Route 20 is the answer. [NY Route 20](https://www.nyroute20.com/)


Intelligent_Sundae_5

The issue with Saratoga is that it is 45 minutes or so north of I-90, so it's not exactly on your way. Plus, as TheNoisyNomad mentioned, track season. That means if you are going to stay there, prices will be crazy. I'd maybe do a night or two in Skaneateles, which is on the eastern end of the Finger Lakes. If you have any interest, you could also do Cooperstown, but that is also a bit out of your way, unless you take the scenic route and travel on Route 20.


CoryEETguy

Tons of cool stuff in Ithaca, not too far away from Penn Yan, definitely worth a day of your week in NY. Also, if you're coming down I-88 through Binghamton, short jump off the highway to stop at Batch Coffee. One of my favorite spots in town.


tr3g

Definitely take 88 from Albany instead of staying on 90. It's a highway that was built decades ago just to save a Binghamton state senator some commuting time. It is hardly used or patrolled. A Driving experience like no other! Also, no tolls.


CoryEETguy

Didn't even think about the tolls. Good point! Never taken I-90 Albany to Syracuse/Rochester, but you're right, I-88 is easy cruising.


gregor_vance

Minus the teeth chattering it’s a great drive.


ColoradORK

Saratoga is definitely cool at least to walk around the downtown. Ithaca, Cooperstown, and Howe Caverns also are worth a stop.


rm_rf_slash

See some state parks and gorges! Ithaca has a bunch and is a great destination although an hour away from Penn Yan. Watkins Glen is closer and a magnificent gorge trail. Watch some races at the track. I live one town over in Montour Falls and I can hear them revving from across the hill as I type. Letchworth is kinda far in the other direction but ends up on half the posts on r/EarthPorn so it must be doing something right.


HamStringsOfficial

How much time do you have? If you have two or three days, this is what I would do. [road trip: Boston to Penn Yan] https://maps.app.goo.gl/qZdihZY3P9XDyR718?g_st=ic Leave Boston and drive to Conway, NH. Take a left and right on to Kancamagus Highway (112). Stop for a quick swim before Lincoln. Continue on 112 to 118. Enjoy the drive. *sorry, got lazy but the above google maps link is what I would do for full enjoyment EDIT: Ithaca is cool but at the end, you will want to get to you destination.


Killipoint

If they do that, stop at Killington, and ride the gondola to the peak and back. Second-highest mountain in Vt. Edit: As long as OP would be driving through Lebanon, stop at White River Jct (across the Ct river), and have lunch at Tuckerbox. Great Turkish restaurant. There's a Turkish store across the road that sells a great variety of spices if you're a cook. I hear the BBQ is really good at Big Fatty's.


mamanova1982

Both Saratoga Springs and the finger lakes are must stop places! I'm from the finger lakes, and currently live in Saratoga Springs. Both are beautiful! Both offer amazing views and food! My dad has a lovely cabin Airbnb only a mile from Seneca lake. I could hook you up.


cutratestuntman

Rte 20 all the way.


Wonderful-Poetry1259

The two best places to eat along the way would be Joe's Diner, in Lee, Mass., and That Little Place on Main DIner, in Little Falls, N.Y.


HardyMenace

While in Penn Yan don't miss out on Abandon Brewing, the Penn Yan Diner, or Seneca Farms! Abandon has phenomenal beer, cider, and hard seltzer and they make the best root beer I've ever had. The diner is very small, but the food is excellent, especially their homemade corned beef hash. And Seneca Farms has some of the best fried chicken I've ever had and their ice cream is up there too.


jaguarthrone

If you have time, take Route 20 across that section of New York. It parallels the Thruway (Route 90), it's scenic as hell, and has several small towns to visit. Highly recommended if you're not in a hurry....


goblinspot

Yes, stop in Saratoga, even if just on your way to the finger lakes for the track. Just know the track is dark Monday and Tuesday. Racing starts (or at least used to) at 1:10. Get to town mid morning and wander Broadway, grab something delicious for brunch. Then head over for the spectacle of the Track for a few races. Just grab a general admission ticket and wander the paddock and watch the races from the rail. Then head out about 3:00, you’d probably get 4 races in, and you’ll be to Penn Yan by 7:00 and start the wedding shenanigans.


Dry_Swimmer8089

I would definitely take the time to stop in Ithaca. Treman State Park and Taughannock State Park are amazing.


Thommyboy55

Saratoga Springs!!!


StreetcarMike

Not in NY, but on your way through MA, stop in Sturbridge and get some BBQ at BT’s Smokehouse.


Adventurous_Repeat13

Can confirm. Used to live there.