6 Themed Itineraries

Itinerary: Classic Williamstown

Not sure where to start your adventures in Williamstown? Here are a few suggestions from locals who love where they live and want to share it with you.

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Where to Stay

Bascom Lodge on Mount Greylock

Top of Mount Greylock

Bascom Lodge is a rustic stone and wood building at the summit Mount Greylock, built by the Civilian Conservation Corps in the 1930s on the Appalachain Trail. It is open from May to October.

B&B: Blackinton-Manor

North Adams

An elegant 1832 Italianate Federal style home, was originally the luxurious estate of wealthy textile manufacturer Sanford Blackinton.

B&B: Ingalls Crossing


Two-bedroom, two-bathroom bed & breakfast apartment on a 700 acre working dairy farm in rural Williamstown.

B&B: River Bend Farm


An authentically restored 1770 Georgian Colonial now a bed and breakfast for history and antique lovers.

B&B: Upland Meadow House


First floor two-bedroom bed and breakfast suite with private entrance, next to Hopkins Memorial Forest.

INN: 1896 House


The 1896 House Inn and Country Lodgings is an upscale three building lodging and dining campus.

INN: The Orchards


Old-fashioned New England elegance with modern convenience that can accomodate an overnight stay, meetings, and weddings.

INN: The Porches Inn

North Adams

Porches’ 47 rooms of retro-edgy, industrial granny chic ambiance make a spirited lodging statement in New England and beyond.

INN: Topia Inn


A 9 room organic inn dedicated to the green lifestyle.

MOTEL: Harwood Hill Motel & Cottages

Bennington, VT

Located on over 4 acres of park-like grounds atop Harwood Hill with spectacular views of Mt. Anthony, the Bennington Battle Monument and Green Mountain vista.

RENTAL: Airbnb

Connecting people who have a place to share with those who are looking for a place to stay.

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Celebration Planner


Farms, museums, mountain tops, and movie theaters — discover the unique locations in and around Williamstown.


Farm to table, elegant canapes, food trucks, and more.


Photographers, floral, beauty, bakeries, and more.

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Find Your Next Home

Alton & Westall Real Estate

Specializes in fine real estate, including homes, acreage, and commercial properties. Licensed in Massachusetts and Vermont.

Bishop West Real Estate

Residential and commercial brokerage licensed in Massachusetts, New York, Vermont, and Florida.

Burnham Gold Real Estate

Services Northern and Central Berkshire County. Specializes in home sales, academic/summer rentals, and commercial properties.

Harsch Real Estate

Locally owned and operated agency with agents who live in the Berkshire County.

Northern Berkshire Cohousing Community

Our vision is to create a community that is multi-generational, mixed income, eco-friendly, accessible to all abilities, environmentally safe for those with chronic health conditions, and honoring of human diversity.

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Shops & Services

Greylock Gallery

Williamstown Cultural District

Showcasing a variety of traditional and contemporary art from both emerging and established artists.

Antiques: Sanford & Kid Antiques Co-op

Downtown North Adams

Two-level, multi-dealer shop featuring antiques, collectibles, vintage, mid century modern, glassware and china, furniture, jewelry, pottery, art, tools, and treasures.

Art: Progressive Palette

Throughout the region

Explore your creativity and artistic expression at a painting or sculpting party.

Co-Working Space: Cloud85

Downtown North Adams

Day-passes available at this co-working space for entrepreneurs, designers, journalists, freelancers, telecommuters and business creators but all professionals are welcome.

Computers: Mad Macs

Downtown Williamstown

Williamstown’s only Apple specialists for sales and service.

Jeweler: Goodman’s

Downtown Williamstown

Jewelry, repair, engraving, trophies, baby gifts, batteries, and more!

Music: Toonerville Trolley CDs & Records

Downtown Williamstown

An independent music store selling new and used vinyl records and CDs. Thousands of out-of-print records in stock and a huge selection of hard to find new and used CDs

Pets: Bark N’ Cat

Downtown North Adams

An independent pet supply store specializing in natural and premium pet foods for cats and dogs.

Pets: Pawnal Pets

Pownal, VT

Full-service pet boarding just over the border in Pownal, VT.

Retail: Amy’s Cottage

Downtown Williamstown

An eclectic boutique featuring an array of gifts and women’s clothing. Featuring Vera Bradley, PANDORA, Burt’s Bees, Fire and Light, April Cornell, and Crabtree & Evelyn.

Retail: Berkshire Outfitters

Adams, MA

The source for name-brand gear, canoes, kayaks, mountain bikes, backcountry, X-C skiing, snowshoeing, running and much more.

Retail: Hudsons

Downtown Williamstown

A unique combination of art, antiques, and collectibles from the region. Specializing in fine and decorative art, jewelry, handbags, Persian rugs, records, guitars, antiques, and gifts.

Retail: Nature’s Closet

Downtown Williamstown

Quality new and used outdoor clothing, footwear, and accessories for active lifestyles.

Retail: Ruby Sparks

Downtown Williamstown

A women’s clothing store: a burst of fashion with the freedom of comfort!

Retail: The Shops @ The Library

Downtown Williamstown

Four unique shopping experiences: gifts and cards, men’s and women’s clothing, Williams College apparel, and antiques.

Retail: Spin-Off Yarn Shop

Williamstown Cultural District

An extensive selection of alpaca yarns and other natural fibers such as wool, cotton, and silk and other natural blends.

Retail: Williams Shop

Downtown Williamstown

The place for all items Williams College! From t-shirts to hats, stuffed animals to swivel chairs.

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Getting Here

Rome 2 Rio

Door to door directions by plane, car, bus, train, and even ferry, with estimated times and costs from anywhere in the world. Also includes hotel listings.


Links to airports that service the Berkshires.

Upstate Green Cab

Appointment-based service between Albany Airport, Bus, Amtrak and Williamstown.

Tunnel City Taxi

6am-12midnight. Service in and around Williamstown and North Adams. 24 hour notice for ride to Albany Airport.

The Spoke

Colonial Shopping Plaza

Large selection of “new old stock” parts, latest models, cutting edge clothing and accessories. Bike rentals.

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Scenic Drives

Mohawk Trail Scenic Byway

Opened in 1914 as one of the first auto-touring roads in the country. Discover the wonders of Route 2.

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