ICONIC BREAKFAST Located just a few blocks from the center of town , you ’ ll find The Blue Benn , one of America ’ s best diners ! This 1947 dining car has everything you want in your breakfast experience : table-top jukeboxes , a huge menu of everything you could possibly dream up for breakfast , and great coffee . Seating is on the honor system , so read the door and then once you ’ re seated make sure to ask for a grilled donut !
Blue Benn Diner in Bennington
HIKE HARMON HILL A short , but intense uphill to some of the best sites in Bennington , just drive 5 miles east on Route 9 ( Main Street ) and you ’ ll see the parking on the north side of the Rte 9 . Cross ( carefully ) and start your ascent to one of the best views in Bennington and get the bragging rights to having completed a portion of the Appalachian Trail ! Then go freshen up .
FARMERS ’ MARKET AND SHOPPING If it ’ s Saturday , you don ’ t want to miss the Bennington Farmers Market which is full of locally-made products , live music and waterside views . From there , just walk into town and stop at some of our incredible shops , including oneyear-old , W . Collective . This hip space is full of home goods , jewelry , decor and flowers sourced locally and from New York . They also have an incredible selection of natural wines ( pick up a bottle for later !), pastries and coffee . Sit out front or in the hidden courtyard out back for the best experience while you refill that calorie deficit ..
PASS THE TIME A playable pinball museum ? Yup ! It ’ s just a little north of Crooked Ram and it ’ s everything you think it is . Play through the decades in this fun space with games honoring favorite places , films , tv shows , bands and more . Just get your lanyard and play as much as you want . Something really fun and different !
BACK FOR DINNER Head back to Bennington and head to Miller ’ s Toll for a cocktail or two and tapas . This spot has a water-side outdoor deck , incredible munchies and stellar cocktails ( along with wine , beer and NA options ). It ’ s beautifully appointed with open areas and more private , plush salons for that old-school feel that will have you thinking you ’ re in Manhattan , not Bennington .
Pastime Pinball in Manchester