Beginning his thrifting at the tender age of 14, Ryan Kennedy was eager to put his stamp on a permanent vessel for his love of iconic rock and roll and the look that goes with it.

The name Sympathy for the Rebel instantly conjures up images of the Stones and James Dean fetishism. From the original art on the walls to the clothing within it, the space oozes Ryan’s personal style and love for a time when music — and especially fashion — were considerably less disposable.

Now in its third year, Sympathy has become Peterborough’s destination for vintage leathers, cowboy boots and pop culture oddities that you’d probably have to visit a hundred antique stores to obtain.

Having expanded to include luggage, cocktail dresses and everything in-between, Sympathy doesn’t bypass trends, but rather looks for staples.

“The idea is to find classic, versatile items so that you can avoid seeing a photo of yourself in five years and say ‘What was I thinking?'” Ryan explains.

Though affordability may have initially drawn him to plant roots on Water Street — as opposed to the more bustling sector on George — Ryan says he has always had an affinity for the area.

“It’s my handwriting that says ‘Push Down’ on the entrance of Needles in the Hay.” Ryan says, referring to when the neighbouring yarn shop was previously Starving Artist Framing Studio, where he worked close to a decade ago. “It’s the surviving details like that which give the strip its character.”

In addition to carrying the torch previously held by businesses like Last Tango, Ryan crafts some of the most innovative contemporary music emerging from Peterborough’s renowned music scene.

January saw the debut of an ambitious series of monthly e.p.s in collaboration with longtime bandmate, Jeremy Boyd. Taking a decidedly minimal approach, the duo’s group Boys Republic evokes the slithering charm of groups like Morphine or Echo and the Bunnymen.

Along with hot spots such as Le Petit Bar, Bloodline Parlour, and Needles in the Hay, Sympathy has helped transform the west side of Water Street into the burgeoning boutique neighbourhood it has become.

Sympathy for the Rebel is open Tuesday to Friday from 11 am to 6 pm, Saturday from 11 am to 5 pm, and Sunday from 12 pm to 5 pm.

Having just recently celebrated their second anniversary, co-owners Linz and Jess Hunt’s Bloodline Parlor makes a dynamic addition to Water Street.

Like the many other unique businesses in the district, the boutique beauty salon looks and feels like the physical manifestation of the artisan denizens that operate it.

Resplendent in leather and silver and oozing nonchalant glamour at the flick of her wrist, younger sister — and avid Kate Moss enthusiast — Linz explains that it was the plethora of terrific neighbors that made the two decide upon Water Street as their permanent locale.

I’m sitting at the front window of The Planet Bakery at 374 Water Street listening to Iris Dement. People are lined up at the front counter buying bread and getting lunch to go.

Suddenly, owner Ted Pearson comes flying into the restaurant sporting his usual attire: a t-shirt and jeans accessorized with a baseball cap. Ted has just returned from working at The Planet Bakery’s second location at Trent University.

The back of the house is packed for the lunchtime rush but Ted ushers me past the crowd through to the kitchen area, hands me a stool to sit on, and immediately begins kneading and portioning dough for tomorrow’s baking.

In 1986, I moved from my parents’ house in the suburbs to the third floor of a warehouse apartment at 393 Water Street.

At the time, I was working as a waitress at Fancie’s Dessert Café, just a few doors down from the massive, sparse, commercial building once home to the local Masonic Order.