Downtown Whitby Neighbourhood Guide: Small Town Charm

Downtown Whitby is a bustling community bordered by Highway 401 to the south, the railroad tracks to the north, Highway 43 to the west, and Rosedale Park to the east. It’s an eclectic mixture of historic buildings, a library, a museum, and a theatre nestled among unique shops, spas, and restaurants.

Whether you’re here for the day, catching a play at the Courthouse Theatre, or browsing the stalls at the Whitby Farmer’s Market, downtown Whitby –with its enchanting village-like atmosphere – will provide you with unforgettable summer day memories.

The history of downtown Whitby can be credited to entrepreneur Peter Perry, who built a general store downtown in the early 1830s at the corner of Brock and Dundas Streets. The enterprising Perry went on to submit a proposal for a subdivision in downtown Whitby in 1840, which is now known as Perry’s Plan.

Downtown Whitby offers quiet and peaceful living with plenty of green space, parks, and playgrounds. The housing in this area will appeal to many architectural tastes and includes century homes, ranch-style bungalows, and side splits, along with newer high-density subdivisions of single detached homes, duplexes, and townhomes. 

The heritage homes in the downtown core feature distinct Victorian architecture, and situated just south of downtown, the Port Whitby Marina features homes with scenic views of the lake. From traditional homes to modern townhouses, downtown Whitby offers something for every taste and budget.

Downtown Whitby has a vibrant arts scene, with artistic murals scattered throughout the downtown area. It’s also known for its events and festivals such as the Whitby Lights The Night and Holiday Festival, Whitby in Bloom, Movies in the Park, and Harvest Festival.

The Whitby Lights The Night and Holiday Festival kicks off the start of the holiday season with a bang, and this year, it ran from November 26, 2021, until January 5, 2022. Spectacular holiday lights twinkle at Whitby Civic Park, Grass Park, and Celebration Square, where a 30-foot Christmas tree towers above the square. Over 100,000 twinkling lights and displays make for an unforgettable winter wonderland!

Also adding to the small town celebrations is Port Whitby, a marina nestled on the nearby shores of Lake Ontario. Here you’ll find a large Canada Day celebration with fireworks and live music.

For theatre buffs, the Whitby Courthouse Theatre, situated in downtown Whitby, offers drama lovers the chance to take in plays, acts, and music of all genres.

Since 1997, local residents and visitors have been enjoying the downtown Whitby Farmer’s Market, currently in Celebration Square, just outside the Whitby Public Library. This market provides a Sunday destination for families and friends, where they can shop for fresh farm-to-table fruits and vegetables, baked goods, and unique handcrafted items.

Downtown Whitby offers an array of shopping venues, with many unique shops. The historical shopping district at Brock and Mary Streets, known as the Verandas of Pearson Lanes, is a charming mixture of boutiques, retail shops, and services.This popular shopping district stretches several blocks in all directions.

Here you’ll find unique independent shops like Soda Pop Central, which specializes in selling soda pop that you won’t find at your local retailers, such as Birch Beer and Green Apple Jalapeno flavours. Woodcraft will appeal to connoisseurs of fine wooden furniture. The store’s solid wood furniture is handcrafted from Canadian trees and includes tables, chairs, and office and bedroom furniture. 

Van Belle Floral Shoppe features artistically designed, colourful, and vibrant flower arrangements that are made-to-order for special occasions – from wedding bouquets and corsages to colourful bouquets of fresh-cut flowers.

Restaurants abound in downtown Whitby. The owner of Pira’s Portuguese Chicken grew up in a Portuguese household in Toronto and was raised with European-based recipes and flavours. The restaurant offers delicious Portuguese chicken, beef, and fish that will feed anywhere from a party of two to a party platter serving 40 people. The restaurant will also cater to your special event and offers delivery to your doorstep.

Since 2005, The Gryphon Pub in downtown Whitby, which is named after the mythical gargoyle, has been a welcoming spot for neighbourhood residents The pub is over 4,500 square feet with an attached outdoor patio, serves up 18 beers on tap, and features entertainment – including karaoke and live music– in addition, to live sports. Pub goers can enjoy a creative menu, featuring breaded pickles, cactus fries, or a veggie omelet in traditional pub surroundings.

If you’re looking for a neighbourhood with plenty of green space, Downtown Whitby will be a favourite destination. The area boasts 10 parks and eight playgrounds, including Regency Park, Rosedale Park, and College Downs Park. 

Whitby Kinsmen Park is located near the downtown core and is a favourite for families with small children with its several slides, swings, and a splash pad. A basketball court and baseball field will appeal to fitness enthusiasts. The park is perfect for strolling with your dog, playing a summertime baseball game, or shooting basketball hoops. You might even try your luck at a game of outdoor horseshoe.

Downtown Whitby offers a range of local parks, complete with basketball courts and softball diamonds for sports lovers of all kinds. Additionally, the neighbourhood is home to 10 local gyms, including Anytime Fitness on Dundas Street West. Enjoy a yoga class or work out with free weights and cardio equipment, and keep fit with friends.

Downtown Whitby is accessible by Durham Transit, with a handy 80 transit stops in the neighbourhood. The Whitby GO Station is conveniently located just south of the neighbourhood and is a five-minute drive from downtown Whitby or a 10-minute bus ride. For commuters wishing to drive into the city, Highway 401 is at the south end of downtown Whitby, and you’ll reach Toronto in under an hour.

Downtown Whitby is a historic hamlet that offers a range of shopping, dining, boutiques, and salons. The downtown museum will appeal to history lovers, and visitors will enjoy a trip to Confederation Square, where they can take in entertainment, festivals, and the Farmer’s Market.

With its charismatic downtown area, Downtown Whitby will appeal to families with its wide range of parks and playgrounds or to singles with its pubs and trendy restaurants. This community offers small-town charm for a day trip away from the city or for a new home in a laid-back community.