From NY to Lake Winnipesaukee
 

I'm traveling this Aug. to lake Winnepesaukee and will be pulling a 16-20ft boat. My question is. Having not been to an area of New England near there for quite some time I can't remember myself. But is it overly hilly in the area surrounding the lake or leading to it? When I go to the Catskills or the Adirondacks there are some wicked hills obviously because there's mountains. I don't remember anything drastic. Just want to be prepared and prep my truck accordingly.

NY to Winni
 

Several questions come to mind. What route are you using?, what part of the Lake are you headed to?, does your vehicle have plenty of power?

If you go across Vermont and enter NH near Keene, you will encounter quite a few hills between there and the Lake, and some tricky driving on narrow roads. If you enter NH on either I-93 or I-95, you will encounter some long uphill grades, but the roads are very good and reasonably well maintained.

If you do some East-West-East driving in NH you will find that those roads are lesser roads, and there could be hills. North-South-North driving is much better up to the Lakes Region, but north of the Lake, in either direction, can be tricky.

New Hampshire is mountainous, not like Rocky Mountains mountainous, but you will certainly notice the terrain.

However, it must not be too bad because I see cars and trucks of every description pulling what appears to be some heavy boats.

Good Luck, enjoy the Lakes Region.

NY To Winni
 

Camp Guy has it pretty spot on. Depends on what part of NY you're coming from. I've pulled trailers from Lake George to the Lakes Region through Vermont and hit some pretty good hills. If you're coming from another part of NY you'll find the ride right down 90 pretty easy. You'll most likely take 90 from NY right into Massachusetts to 495 North, to 93 North right into the Lakes Region. Easy ride when pulling a trailer. Just time it right so you avoid the heaviest travel times.

Good luck and enjoy the beautiful lakes region. Make sure to have a chart or GPS if you're planning on putting your boat on Winni! If you don't have a chart you can purchase them at a lot of different places once you get up here.

From LI
 

We haul our 16' Whaler up and back at the beginning and end of the summer from Long Island. Also dragged our 20' Key West up there 7 years ago when we bought our place on the Lake. It's a pretty easy route overall. Some hills along the way but nothing too terribly steep. Just follow your usual precautions and make sure your vehicle's brakes are in good condition as there can be a lot of stop and go due to traffic.

What are you driving and what's your route?

LI to Winni
 

I've done the ride close to 100 times in the past 8 years and 10 with a 30 foot Skater in tow. Take the Bridgeport Ferry, even with the boat. Saves a tremendous amount of time, traffic and aggravation especially traveling through the Bronx, Westchester and Southern CT.

Plenty of room on the ferry just make sure you make your reservation in advance, they tend to book quickly in the summer on weekends.

As mentioned above make sure your brakes are in good shape and you will be fine, its not a bad ride especially once you get onto Route 91.

Gook Luck.