Which town in the Berkshires
 

We're planning a driving trip in NE in August. We'll be leaving from NYC and thought about someplace in the Berkshires for the first couple days. We'd like to drive 2-3 hours when leaving NYC. While there we'll probably drive through small towns, enjoy the scenery and maybe hike. What about places to stay? We like small B&B's. Pricewise around $200 or less would be nice! Thanks!

Would recommend Lenox / Stockbridge but you may find them to be more than $200 and have minimum night requirements

You sound like you want New Milford, New Preston and Litchfield, CT

tchoiniere-definitely hard to find a place that will take us for just 2 nights and most seem to be upwards of $200.

sobster - will check out the towns u mention. I know Litchfield is a bit South of Lenox. Do u know about how far it is? thanks

Although I am familiar with the Berkshires and prefer to stay in small B+Bs, I have not stayed in a small BB there. (I have friends that I stay with) However, you might take a look at the Shaker Mill Inn in West Stockbridge http://shakermillinn.com They appear to take 2-night reservations during the summer and the location will put you in South county close to Tanglewood, Jacob's Pillow, and Theater. West Stockbridge will put you within easy access of the Mass Turnpike as well as charming country roads. For a more comprehensive listing of small B+B's it is always a good idea to check the local Chamber of Commerce sites since many small lodging places advertise there but can not afford to buy into the larger 3rd-party travel sites that you may be used to using. In this case go to the Stockbridge Chamber of Commerce site: http://www.stockbridgechamber.org/where_to_stay.htmland you will see a variety of lodging that might work for you! Let us know where you might be going after the Berkshires if you need more "small town" suggestions.

yellowbird -- thanks, will add those ideas to my searching. I think we may go over to the Hudson Valley area. Any recommendations for towns to stay in over there?

Litchfield is substantially south of Lenox. We used to call that area "the foothills of the Berkshires." You might look at Williamstown, MA

Take a look at Chatham, New Lebanon, and Spencertown on the NY side of the Berkshires. Lots of B&Bs there. Churchill House and Spencer House would meet your price point as would Spencertown Cottages. Those are but a few. We lived both in Spencertown and New Lebanon and can attest to the beauty and charm of the area. Stockbridge and the rest of the Berkshires are a short drive away. Pittsfield Mass is just over the mountain from New Lebanon and Stockbridge about 15 minutes from there.

Thanks everyone for all your suggestions. We're thinking of staying in Lee, Mass at a relatively new B&B Collins House. That an okay town? It's close to Stockbridge and Lenox.

Lee is in a perfect location. Easy drive to Lenox and Stockbridge. That B&B is in a good quiet location. For hiking near there, I would recommend Monument Mountain (off of Rt 7 South) towards Stockbridge. Its an easy hike with a great view at the end

Not sure if you are interested in staying in North County .. but lots of people seem to love Porches in North Adams .. It is within walkable distance to MASS MoCA .. The Clark in Williamstown .. Williams College .. and lots of theatre .. About a forty-five minute drive to South County .. and if you should go to Lee .. check out Chocolate Springs .. great chocolates and wonderful pastries ....

tchoiniere, thanks for the feedback on the location of Lee.

mahs, we looked at staying in the North County and Porches was certainly appealing. But we will be leaving early from DC, stopping off in NYC and then on to the Berkshires. So we figured we'd be better off staying in the Southern portion given the distances we'll be driving that day. From googling the distances it was about 45 minutes difference to drive up to N Adams area.

We have stayed in Lee many many times, as we have friends who live there. Little town very convenient to Tanglewood and other Berkshire attractions. There is outlet shopping, if that's your thing. The famous "Joe's Diner" of Norman Rockwell fame is in Lee. There a stretch of "town" that is literally like 2 long blocks long. Movies are located a little north in Pittsfield (either the small museum theatre or the mall) or south in Great Barrington, maybe 15-20 minute's drive. We love the funky vibe of GB. Lee is quieter. Nice little Sandy Beach Lake in Lee. Plenty to do. Don't know if you will be able to stay only 2 nights. Often there's a 3 night minimum, in season. Good luck. There's mucht to do in the Berkshire. Antiquing. Theatre. Museums. Dance.

I second everything Native NewYorker said. Lee is a great little town located perfectly so that you are near Lenox, Stockbridge and Great Barrington. Also - if you enjoy antiqueing, there's sheffield right on the other side of Great barrington. You will love the area and this is "the area' of the Berkshires. Definitely do a show at Tanglewood and also be sure to eat at Babba Louie's in Great B. for amazing organic pizza and salads, and for our fave gourmet restaurant, (it's a splurge but well worth it) go to Zinc in Lenox!

Thanks azh111 & others--we will be staying in Lee

Good choice! The town of Lee is not nearly as nice as Lenox or as funky as Great Barrington, but it is still quaint and perfectly located. Be sure to go to the Cakewalk bakery right on Main Street for the best scones, muffins and cookies anywhere!

We spent many summers near Great Barrington, of which I have fond memories. I have not been there isn 25 years, what is the town like these days?

ahhhh...Cakewalk bakery, got it! Thanks again

One relatively reasonable B&B right in the heart of Lenox is the Cornell Inn. My husband and I got married in Lenox three years ago, and reserved a block of rooms at the Cornell Inn for some of our guests - if I remember correctly, rooms back then were around $135/night (in September). The guests thought it was very charming and quite nice. The Village Inn in Lenox might also have some reasonable rates, possibly under $200.
Our favorite restaurants in the area are in Great Barrington: Baba Louie's (wonderful, top-notch gourmet pizza); Allium (slightly upscale, but delicious, with lots of locally grown fare); and Pearl's (also slightly upscale, but consistently delicious)! For more casual fare, and decent seafood, we also recommend Salmon Run in Lee. For a fun "greasy-spoon" experience, try Joe's Diner in Lee (great cheeseburgers), or go for breakfast at Martin's in Great Barrington (very popular breakfast/brunch spot).
My husband and I go up to the Berkshires as often as we can - it's a wonderful, beautiful, special place! We also recommend a concert at Tanglewood (enjoy a picnic dinner under the stars!), the Norman Rockwell Museum, and a beautiful and easy hiking trail starting at Olivia's Outlook (spectacular view!).

Kem513 -- thanks for all your recommendations. Looks like there are plenty of good placs to eat. We did find a B&B in Lee that we will be staying in.