Less than 2 hours left of Boston, Greenfield is the gateway to the Berkshires and Western MA (depending on which way yr going).  Route 2 is a nice drive, especially during this time of the year!  Here’s a loose top 5 for free and cheap hangouts in Greenfield, the up and coming northern bastion of the valley.

1. POET’S SEAT TOWER mountain road

A sandstone observation tower erected in 1912 to honor one of local poet Frederick Goddard Tuckerman’s favorite spots, offering amazing views of the town, nearby village Turner’s Falls and beyond.  Tuckerman dubbed the crag “poet’s seat” in 1850 and a wooden tower preceded the stone one.  Aside from the paved road, a number of trails about 1-2 miles in length wind up to the summit.

2. JOHN DOE JR. 269 main street

One of the best vinyl shops in the Pioneer Valley, JDJR deserves a comprehensive dig from a-z, the gems don’t dry up.  Always fair, sometimes obscenely low prices.  Nice cassette and book selection as well + an occasional in store performance.  Say hi to Scott, he’s the best.

3. BRASS BUCKLE 204 main street

Excellent gourmet sandwiches + salads, breakfast served all day and inventive menu items in the brunch zone one may have never once thought of before the bucklers.  The perfect accompaniment to a pre/post JDJR visit.  I hear Anthony Bourdain was there recently.

4. GREEN RIVER RECREATION AREA nash’s mill road

A straightforward swimming area with facilities, lifeguards and trails.  Can get pretty crowded on a hot day.  There is a sand beach on one side of the river and a stone retaining wall on the other with ladders providing access to the water.  There are also public charcoal grills!  Across the road is a choice section of the bike path.  Biking in Greenfield is highly recommended.

5. EUNICE WILLIAMS COVERED BRIDGE SWIMMING SPOT (disclaimer: *spooky*) eunice williams drive

On a more secluded section of the Green River sits a beached covered bridge in a state of disrepair.  A nearby plaque tells the story: in the Deerfield Massacre of 1704, 54 were killed and some 109 captives of the French/Native American militia were marched north into Canada.  At this spot, Eunice Williams, wife of captive Reverend John Williams was killed at this place, “hacked in the river”, some sources say days after giving birth.  It is believed that when the covered bridge stood, Eunice could be summoned by stopping inside the bridge, turning off the headlights and beeping once.  Best swimming: the base of the waterfall.

RUNNERS UP: Federal Street Books, Replay, Mag Pie, Pale Circus, Greenfield Coffee, Old Greenfield Village, Green Fields Co-op