ITINERARY : HIP EATS , DRINKS , HIKES , ADVENTURES AND WHERE TO SNAG THE BEST PHOTOS FOR SOCIAL
ICONIC BREAKFAST Located just half a mile north of the center of town , you ’ ll find The Blue Benn , one of America ’ s finest and most famous diners . This 1957 “ Silk City ” dining car has table-top jukeboxes , a huge and creative menu , and bottomless coffee . You may have to wait in the vestibule for a booth ( even Gwyneth Paltrow waited ) , but you can always sit at the counter if there ’ s room .
HIKE HARMON HILL For a short , but intense uphill to a fine view over Bennington , drive 5 miles east on Route 9 ( Main Street ) and pull into the parking area on the north side of the road . Cross to the south side ( look both ways ) and begin your ascent . The stone stairs look natural but were actually laid by stalwart trail builders in the 1970s .
FARMERS MARKET AND SHOPPING The Bennington Farmers Market has moved south of town , but the new Community Market on West Main stocks local produce ( and uses it in their prepared foods , too ).
HEAD NORTH , YOUNG MAN In fact it ’ s fun for all ages at Pastime Pinball , a playable pinball museum in Manchester , just north of the Crooked Ram . Play through the decades with games honoring favorite places , films , TV shows , bands , and more . Just get your lanyard and play as much as you like . It ’ s addictive – but harmless !
BACK FOR DINNER Head back to Bennington for a drink and a bite at the Miller ’ s Toll . This spot on East Main has a water-side outdoor deck , tempting small plates , and stellar cocktails ( along with wine , beer and NA options ). Quirky interior spaces , too .
From top : Photo courtesy of Blue Benn Diner in Bennington and photo courtesy of Pastime Pinball in Manchester