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Things to do in the Pioneer Valley and Five Colleges Area


The top area attractions in Pioneer Valley, MA.

The Five College Area is home of Amherst College, Mount Holyoke College, Hampshire & Smith Colleges, and The University Of Massachusetts, Amherst.

Situated in the larger area of the Pioneer Valley — the area of fertile farmland and first settlements along the Connecticut River — this expansive scenic region is known for both its brains and beauty. There's more than just intellectual ventures here: this versatile region offers rural country land and busy urban cityscape, as well as world-class cultural destinations and outdoor adventure.

With lots to do and much to see, you'll want to have cozy and convenient accommodations. The Five College Area Bed And Breakfast Association is passionate about hospitality and anticipating our guests' needs, delivering everyday comforts with personalized service at our crisp and clean accommodations.

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The best places to stay & visit in   Pioneer Valley

The Town of Amherst, located in the lovely Pioneer Valley of Western Massachusetts, is a diverse, inclusive community offering numerous educational and cultural opportunities.
Host to Amherst College, Hampshire College and the University of Massachusetts, Amherst is bubbling with culture, art, music, and theater. See a show at the UMass Fine Art Center or the Northampton Center for the Performing Arts, catch a live music performance at the Mullins Center, savor beautiful art in one of the many surrounding museums or just appreciate history in the Emily Dickinson Homestead.

The Town of Belchertown is the eighth largest town in area in Massachusetts. The town common, lined with churches and colonial homes, is the site of band concerts, festivals and community activities throughout the year. The Belchertown Fair, one of the oldest continuously operated fairs in the country, takes place on the common each October. Belchertown is the home of the Quabbin Reservoir, a popular place to fish and hike amongst the half million yearly visitors. The Stone House Museum is a gracious 1827 stone structure containing period Connecticut Valley antiques and furnishings.

The Town of Chesterfield is a rural agricultural hilltown located between Northampton and Pittsfield. The town was laid out in 1739 and sites were granted to King Philip's and King William's war veterans in 1740. The town center was established after the Revolution with well preserved Federal Period houses along Main Road and landmarks of civic buildings in a later Greek Revival style.
Chesterfield is located only 12 miles from Smith College in Northampton, and within a reasonable driving distance (30 min.) from Amherst, Deerfield and the Berkshires of Western Massachusetts.


The city of Easthampton, once a small New England manufactering community, is now a vibrant diverse destination with an emphasis on the arts and recreation activities. Renovated mill buildings and a revived downtown center now feature critically acclaimed restaurants, galleries, cafes, and entertainment for everyone of all ages.

Opportunities for recreation include the 6 mile Manhan Rail Trail, Nashawannuck Pond with a new Promenade, Arcadia Wildlife Sanctuary for birdwatching, and Mount Tom State Park for hiking trails.
Easthampton is also the home of Williston Northampton Academy, one of the top college prep schools in the country.


Enjoy gently rolling hills dotted with farms; fresh produce and flowers in summer as well as fields for berry picking; the Heirloom Tomato Festival at Red Fire Farm; or choose from 150 flavors of ice cream at Cindi's old-fashioned Drive-In. Deep woods with meandering trails abut the the Notch and Mt. Holyoke State Park. The many maple trees create a glorious fall foliage display. Granby is also home to the prestigious MacDuffie School, and borders Mount Holyoke and Hampshire Colleges (the Eric Carle Museum and the Yiddish Book Center). The local Dufresne Park hosts numerous regional horse and dog shows as well as Granby Charter Days. Granby's central location affords ease of access to all area colleges and other points of interest within the Pioneer Valley, as well as points south and east.


Greenfield was first settled by the English in 1686 as part of Deerfield, and in 1753 was incorporated as a separate town, named for the Green River. It was the eastern terminus of the Mohawk Trail, a principal route for settlers traveling west into Upstate New York.  After the Industrial Revolution, Greenfield was a center of industry, focused on paper production and cutlery factories. It was home to Lunt Silversmiths until 2010, and streets of stately manors are a reminder of a bygone era of prosperity and growth. Today, Greenfield is a residential community with a country feel and is the seat Franklin County, established in 1848. That same year, the first Franklin County Fair was held, and the area is still know for agricultural production.  Greenfield is located at the crossroads of Interstate 91, Route 2 and the famous Mohawk Trail in Western Massachusetts, close to the borders where Massachusetts, Vermont, and New Hampshire meet. The town hosts the annual Green River Festival in July, as well as weekly Farmers Markets on Sundays. Greenfield is within a reasonable driving distance from Northampton, Amherst, Deerfield and the Berkshires of Western Massachusetts, and has an up-and-coming arts scene with the establishment of Hawks and Reed Performing Arts Center. 


Hatfield is a charming rural community of about 3300 citizens, founded in 1670 on the west bank of the Connecticut River. It is 25 miles north of Springfield and 100 miles west of Boston, in the "Pioneer Valley" of Western Massachusetts - a diverse, culturally rich area recognized for outstanding educational opportunities, the arts, outdoor activities, and beautiful surroundings. The Town of Hatfield is known for its rich agricultural history and close-knit community, as well as local pride in and commitment to carrying its farming heritage into the present. Visitors to Hatfield will notice the diverse offering of fresh local produce for sale at many small roadside farm stands, as well as beautiful examples of historic houses and farms lining Main Street and dating back to as early as the late 17th century. With a bucolic feel and slower pace, it can be easy to forget that Hatfield is only 6 miles from Northampton, a celebrated arts and entertainment destination that has been named "Number One Best Small Arts Town in America" and one of the "Top 25 Arts Destinations" in the nation by American Style magazine - as well as being home to Smith College and the center of the "Five College Area."


Haydenville is a village nestled within the lovely New England town of Williamsburg, Massachusetts, just minutes from Northampton. Williamsburg is home to the historic Brewmasters Tavern and the quaint Williamsburg General Store, a historic museum, and The Snow Farm.

Haydenville is surrounded by the lovely towns of Northampton and "the Hilltowns" of Goshen, Chesterfield, Cummington and Ashfield. There are many lovely country roads and woodland trails to explore either on foot, bike, cross country skis or snowmobile or by car.


Northfield is popular for year-round outdoor activities, from paddling, fishing and boating on the Connecticut River, to cycling on the county bikeway, hiking on the New England National Scenic Trail, and cross-country skiing, snowshoeing and river cruises at the Northfield Mountain Recreation and Environmental Center. Northfield's historic Main Street contains some of the best-preserved examples of Federal, Greek Revival and Gothic architecture anywhere. The Moody Center and the New England branch of Thomas Aquinas College recently opened on the campus of the former Northfield Seminary. Our walkable village offers an ice cream shop, a B&B, a deli, an old-timey diner, auction house, art gallery and a winery. Just over the river from Northfield are Northfield Mount Hermon School in Gill, Mass., and the world headquarters of Kringle Candle Company and the Crumpin Fox Golf Club, one of the top 100 small courses in the U.S., in Bernardston. Twenty minutes south on Route 63 is the UMass Amherst campus and, from there, the other colleges in the Five College consortium.


The Town of South Hadley Massachusetts is a small friendly college town located along the banks of the Connecticut River. It is bordered by Hadley and Amherst on the north, Granby on the east, Chicopee on the south and Holyoke on the west.

South Hadley has a relaxing country living appeal and offers a variety of recreational activities from hiking to boating to skiing as well as quaint shops, restaurants, theaters and cafes. It is home to Mount Holyoke College which is one of the nation's finest liberal arts institutions for women.


The Town of Whately was settled in the 1600's, in an area along the Connecticut River that belonged to the Norwottucks, or Fresh Water Indians, under Chief (Sagamore) Quonquont. Whately is located minutes from Yankee Candle, Historic Deerfield, Deerfield Academy, Eaglebrook School, U-Mass, Smith, Amherst, Hampshire and Mount Holyoke Colleges. Nearby Williamsburg and Northampton, offer eclectic shoppes, art galleries and museums, music venues and exceptional dining.

Whately is the home of the Smith College Observatory on Poplar Hill. The observatory is used by the students of the Five College Program, including Amherst, Hampshire, Mount Holyoke, and Smith Colleges as well as the University of Massachusetts.


Williamsburg is a picturesque and historic New England town situated in the foothills of the Berkshires only fifteen minutes from Northampton and Smith College. The town offers several eating opportunities, a market, and a charming general store, along with a library, church and museum. Its close proximity to Amherst, Northampton and I-91 make it an ideal location within a relaxing country setting.
A popular four seasons outdoor recreational area,Williamsburg is just ten minutes from the DAR State Forest and Chapel Falls Trustees of Reservations. Snow Farm, the renowned New England Craft Program is two miles northwest of the town center.
The town is graced with lush hills, pastures, and farmlands yet an easy one hour drive from the culture of Lenox and Stockbridge. Edith Wharton's The Mount, Tanglewood, and Chesterwood are just a few of the many cultural possibilities found there. Jacob's Pillow Dance Festival in Becket is also an hour drive away.