Toronto has officially shaken off its staid old uptight reputation and has joined the brat pack of cool cosmopolitan cities.

None other than the Huffington Post has recently named Toronto as the new capital of cool. In an article posted on the web’s most popular online newspaper, Lauri Lyons wrote, “Toronto is the hot new destination for all things crazy, sexy, cool.”

GirlsGetaway asked, “What’s so cool about Toronto?” We decided to find out, and share with you, what we consider to be Toronto’s newest hippest districts:

Distillery District

A new, up and coming area of Toronto is the Distillery District. The Distillery District is the site of the defunct Gooderham and Worts whiskey distillery. This national Historic Site has kept and restored much of its beautiful architecture and cobblestone streets and now has the largest and best-preserved collection of Victorian Industrial Architecture in North America.

It has recently been named the ‘hippest address in town’ by Toronto Life magazine. The Distillery District’s mission is to develop the area as Canada’s premier arts, culture and heritage precinct. It houses some of the city’s best restaurants, local artists, crafts, galleries, and music.

Where to Shop

SOMA Chocolates

We consider SOMA to be THE best chocolate shop in the city. If you worship chocolate this is the store for you. The tiny (but charming) café has a large glass wall that allows customers to watch as professional chocolate makers produce chocolate heaven right from the bean. Our favorite is the Cherry Bomb truffle but the Mayan hot chocolate is to die for!

Bergo

Featuring the creations of internationally recognized designers and architects, such as Phillippe Starck, Frank Gehry, Karim Rashid and Michael Graves, Bergo is a mecca of industrial design. Everything in this store is perfection in design from ice cube trays to fireplaces.

Distill

With its mandate to show emerging Canadian artists/craftspeople/designers, Distill is one of the best spots in Toronto to find unique, locally and responsibly handmade works, including ceramics, glass, textiles, paintings, jewelry, fashion and accessories. Our favorite find: The subway bracelet. This awesome piece of Leslie Jones jewelery is inspired by Toronto’s subway stations.

Where to Eat

Mill Street Brewery Pub

Voted the best brew pub in Ontario in 2010, this casual and fun spot boasts an impressive inhouse brewery. Try Mill Street Pub’s famous nachos or lobster grilled cheese and of course a pint of Tankhouse Pale Ale.

Brick Street Bakery

The Brick Street Bakery doesn’t have inside seating but don’t let that stop you from trying out some their yummy treats. Best bets are: Boxing Day sandwich, sheppard’s pie, curried sweet potato soup, eccles… I could go on all day!

When to Play

Summertime is the best time to head over the Distillery District; you can stroll through the cobblestone streets and check out the many outdoor booths selling all sorts of cool and unusual items all made by local artisans.

The Distillery District also hosts tons of great festivals and events throughout the summer. Here’s what’s happening this fall in the District:

September 24 – 26 Distillery Art Market 11am to 6pm

October 1 – 3 Distillery Art Market 11am to 6pm

October 2nd Nuit Blanche

October 8 – 10 Distillery Art Market 11am to 6pm

October 15 – 17 Distillery Art Market 11am to 6pm

October 22 – 24 Distillery Art Market 11am to 6pm

October 29 – 31 Distillery Art Market 11am to 6pm

Kensington Market

Kensington Market is not as shiny and polished as the Distillery District but it has a neat gritty feel to it, sort of an old hippy vibe. The small cluttered streets are filled with everything from little cafes, old European fruit and food markets to some of the funkiest retro clothes stores around. If you’re looking for great eating and some exciting (if slightly eccentric) shopping, Kensington Market is your best bet.

Where to Shop

Blue Banana

Kensington’s Blue Banana Market claims to turn “seen it, have it, bored with it” into “love it, want it, gotta get it”

We agree!

This market-style shop features one-of-a-kind items from more than 150 local artists. A trip to the Blue Banana is guaranteed fun, with its two floors of quirky, cool, kitschy and hip clothing, furniture, jewelry and art, the store is full of things we can’t imagine not having.

Courage My Love

A long-time favorite shop of retro shoppers in Toronto, Courage My Love has been a Kensington fixture since 1975. This boutique is a gem, vibrant with quirky, vintage and fun fashions. If you’re ever in need of vintage gloves in shocking pink, a piil box hat, or a go-go dress, you’ll find it here. Our favorite find: an entire wall of buttons, who knew buttons could be used as wall art?

Where to Eat

Supermarket

Asian fusion cuisine. I know… been there, done that, but mix in some Kensington grunge and funky fun like Chatroulette Bingo and this place rocks! Don’t forget to order the OMG so good banana spring rolls dipped in chocolate sauce.

Grilled Cheese

Mmm, melted cheese heaven! What could be better than an entire menu composed almost entirely of grilled cheese sandwiches? Our pick: Grilled Motzy with fiore de latte, basil pesto and sun-dried tomatoes. 66 1/2 Nassau St (647) 347-7062

When to Play

During the summer, on the last Sunday of each month, the market streets are closed to car traffic and fill up with people, music and dance. Organized by the residents and business owners of Kensington, Pedestrian Sundays is a giant neighborhood block party and the entire world is invited to join in on the fun.