Road trips and weekend getaways aren't only for the summer. If you're looking for the perfect destination to escape to this fall, whether for leaf-peeping or a digital detox, look no further than the Berkshires region of Massachusetts. With its colorful foliage, quaint towns and acres of rolling farmland, it's the epitome of autumn on the East Coast. Here's exactly where to stay, what to eat and how to play in the Berkshires.

Where to Stay

Red Lion Inn


Hotel on North

A blend of classic Berkshires ambience and cosmopolitan style, Hotel on North is a boutique hotel located right smack in the center of the region, making it a convenient home base. This restored 1880s building includes an art gallery, quirky restaurant and individually decorated guest rooms for a custom experience down to the very last detail. 

297 North St., Pittsfield, MA 01201. +1 413-358-4741; hotelonnorth.com 

 

Red Lion Inn

This iconic and luxurious hotel in Stockbridge has been in business since 1773, offering both traditional hotel rooms and private cottages decorated in an elegant, old-fashioned style. While the Red Lion is filled with antiques and old-world charm, it's definitely not retro in one important way: The hotel is recognized for its very modern sustainability practices

30 Main St., Stockbridge, MA 01262. +1 413-298-5545; redlioninn.com


Where to Eat & Drink

Mezze Bistro + Bar


Mezze Bistro + Bar

This onetime Moroccan spot is now a nouveau American farm-to-fork restaurant where executive chef Nick Moulton sources local ingredients, from apples to chickens' eggs. Expect a highly seasonal menu with dishes like kabocha squash soup, a celery and kohlrabi Caesar salad, and steelhead trout with a winter squash puree and fried sage.

777 Cold Spring Rd., Williamstown, MA 01267. +1 413-458-0123; mezzerestaurant.com

 

Eat on North

The eccentric eatery inside Hotel on North serves breakfast (don't skip the buttery croissants), lunch and dinner featuring a globally inspired and locally sourced menu. Slurp down freshly shucked oysters at the bar and sip beers from nearby breweries in a fun yet sophisticated atmosphere.

273 North St., Pittsfield, MA 01201. +1 413-553-4210; hotelonnorth.com

 

Bright Ideas Brewing

Given the emphasis on all things local, it's only right that you check out Bright Ideas Brewing, which uses hops grown in, yes, the Berkshires. Go in for a tasting flight of four brews for just $12. Pro tip: Try the Bumpkin, an ale that incorporates pumpkin and butternut squash, and the Wheat, which offers flavors of lemongrass and blood orange.

111 Mass MoCA Way, North Adams, MA 01247. +1 413-346-4460; brightideasbrewing.com 


Where to Play

Cricket Creek Farm


Antiques Shopping

The Berkshires region is a dreamy destination if you're fond of foraging for vintage wares. Visit Berkshire Home & Antiques to invest in (or just admire) everything from an 18th-century armoire to Russian samovar lamps.

107 Stockbridge Rd., Great Barrington, MA 01230. +1 413-429-6317; berkshireantiques.com

 

Monument Mountain Trail

Climb this gorgeous hiking trail for views of the Housatonic Valley. Inhale the fresh mountain air and enjoy some fun outdoors while the temps are still mild.

Route 7, Great Barrington, MA 01230

 

Cricket Creek Farm

The Berkshires are home to a plethora of farms, orchards and markets. Visit Cricket Creek Farm to stock up on products like meats, cheeses, sourdough bread, maple syrup and gooey cinnamon buns. 

1255 Oblong Rd., Williamstown, MA 01267. +1 413-
458-5888; cricketcreekfarm.com

 

Mass MoCA Museum

The Massachusetts Museum of Modern Contemporary Art, which opened in 1999, exhibits work by both well-known and emerging artists. It features large-scale, immersive installations and embraces all forms of art, from dance and music to painting and sculpture. 

1040 Mass MoCA Way, North Adams, MA 01247. +1 413-662-2111
massmoca.org


By Angelina Zeppieri

Angelina is a ​lifestyle writer and explorer from New York City, focusing on travel, food and other important things. You can usually find her on a yoga mat, at a wine store or off on a new adventure. Follow her on Instagram and her blog.