New England Road Trip Hiking?

February 22, 2011 8:26 PM

The breadth of Long Island up to Connecticut, then over to Cape Cod, then up to Boston, and then back to NYC. Where are the best hikes? What do I have to stop and see (and eat) in between the cities? Where can I stay on the cheap?

We are road tripping this route in just a few days here and hoping to do some good hiking along the way, eat some good food in the middle of nowhere, and not spend a lot of money. Any and all advice is greatly appreciated!

Also: is Nantucket worth it in March?

posted by ztdavis to travel & transportation (7 answers total)

Middlesex Fells north of Boston is real pretty. Mashomack preserve on Shelter Island (between the two forks of LI, accessible by ferry) is also nice. Both are more like woody nature walks than true hikes, but both are quite nice.

For food, Greenport (near the end of the North Fork) has a couple really good restaurants--Noah's, Frisky Oyster, Farmhouse.

MeMail me if you need any more info. I grew up on the east end of LI, but I live in Boston now, so those are my present areas of expertise.
posted by weaponsgradecarp at 9:40 PM on February 22, 2011

The trails in the Provincetown part of the Cape Cod National Seashore are astoundingly pretty, but may be blustery in March.
posted by ldthomps at 6:18 AM on February 23, 2011 [1 favorite]

I second the national seashore. It will be cold though, but it is gorgeous. Any of the beaches along the way to Provincetown. Marconi is a real nice one. Not much for hiking, more like just walking on the beach. Check out Cahoon Hollow too.

Provincetown is a great quirky little town but you are still going in the winter so a lot of the better known food options on Cape Cod will still be shuttered for the season. But I found a thread on chowhound with winter recommendations for food all over the cape: Chow Hound

After reading the thread I can vouch for Misaki in Hyannis. Amazing sushi and not too pricey in the off season. Also in Hyannis is the Naked Oyster which has a raw bar with local offerings. Not cheap but good for a cocktail and a few oysters. For food in PTown check out Cafe Heaven for brunch, and the Portuguese Bakery for the malasadas. Not sure about lunch dinner options.
posted by WickedPissah at 7:22 AM on February 23, 2011 [1 favorite]

Are you taking the east end ferry to conneticut or are you taking the NYC route?
posted by majortom1981 at 9:36 AM on February 23, 2011

I'm a huge fan of both Bear Mountain (the tallest peak -- although not the tallest point -- in Connecticut) and Mt. Greylock (the highest point in Massachusetts). The former has a six-mile loop that a couple good hikers can do in a morning. And the latter has a ton of different trails, but it's pretty easy to make a whole day of it. Especially if you go after Memorial Day, so you can go up the memorial on the summit.
posted by Plutor at 9:45 AM on February 23, 2011

Connecticut isn't known for tall peaks, but Sleeping Giant State Park isn't far from 95 (assuming that's your route) and has a neat little tower on top.
posted by troywestfield at 9:49 AM on February 23, 2011

We are taking the east end ferry out of Orient Point.
posted by ztdavis at 9:48 PM on February 27, 2011