With a new purchase in hand, a young woman leaves Out of the Blue, a hot spot for indie fashion. She crosses the street and heads into Kawaii Crepe, a funky eatery serving Japanese-style hand-rolled crepes. Meanwhile, a sidewalk busker with an acoustic guitar rocks an original tune, while his case lays open for donations. This is a small slice of life captured on one sun-drenched afternoon in Winnipeg’s Osborne Village.

The neighbourhood, located just south of downtown Winnipeg and bordered by the Assiniboine River, has been a hub of boho chic since the 1960s. In May 2012, it was named Canada’s best neighbourhood. The area has tattoo parlours neighbouring venerable churches beside a health-food store. Yoga studios, spas, cafés, vintage boutiques, clothing and accessory shops and designer jewelers line the sidewalks. Business has also made itself comfortable in the Village too. Architecture firms and multi-media and entertainment companies have all set up shop in the area.

Osborne Village’s main drag is a buzz of constant activity from sunrise to last call. But walk one block east or west from Osborne Street and discover quiet tree-lined, residential streets. Turn-of-the-century Victorian homes, many converted into multi-use apartment buildings, sit beside upscale condominiums. More affordable rental suites and lower-cost housing are also in the mix.

Where to Stay

Submerge yourself in Village life at a local bed and breakfast. Check out the options at Airbnb. Downtown is also a short walk from the Village, just over the Assiniboine River. The Fort Garry Hotel, a 99-year-old hotel on Broadway and one of Canada’s original “railway” hotels, is an affordable but luxurious experience.

Where to Eat

Stella’s Café & Bakery is a charming all-day breakfast, lunch and dinner spot. Baked Expectations is a popular café and dessert spot known for its epic sweets menu. (The cherry cheesecake is incredible.) Segovia, a Spanish tapas bar and restaurant serving some of the most innovative plates in the city, is one of Winnipeg’s best and busiest restaurants. (Arrive at 5 p.m. on Friday and Saturday nights to ensure you get a table. They don’t take reservations.) Nuburger offers gourmet, healthy burgers while A Little Pizza Heaven is truly a local favourite for late night (or really, anytime) pizza.

Where to Shop

Find unique gifts, home decor and fashion at Style Bar, Hush and Shout and Out of the Blue. Hop over to The Happy Cooker, to stock up on on-trend kitchen and cookware. Stop in a modernist jewellery shop, David Rice for a one-of-a-kind pieces. Pick up a new pair of chic shoes at Rooster.

What to see

Browse the art at Medea Gallery, a co-op featuring works from local artists and artisans. See the extraordinary stained glass windows at St. Luke’s Anglican Church, one of the neighbourhood’s historic churches. Inside The Gas Station Theatre, the venue hosts live theatre, dance and special performances, including comedians during the Winnipeg Comedy Festival. An outdoor graffiti gallery decorates the theatre’s outdoor plaza. On Canada Day, the entire strip turns into a street party with vendors, food and concerts.

For a full list of businesses and restaurants click here.