When you walk through Picton, you can just feel the history. Settled in the 1780’s by United Empire Loyalists and incorporated in 1837, Picton oozes a rich Loyalist heritage. On the grounds of the Armory, you’ll find a statue of John A. Macdonald (Canada’s first Prime Minister) commemorating his time as a practicing lawyer in Picton. From the stunning Loyalist architecture of the public buildings to streets lined with character-filled homes dating back to the late 1800’s and early 1900’s to the abandoned Royal Air Force and Gunnery School, the streets of Picton tell a story about Canada’s past at every turn.

Picton is the County’s largest community, with a population of just under 5,000 residents. The local BIA astutely describes Picton as “a rural community with an urban, neighbourhood feel’.

The Rural Part

Picton’s industry runs on tourism, agriculture and wine…in that order. Enjoy Picton’s plentiful green spaces, with eight municipal parks, including the MacCauley Heritage Park that’s definitely worth a visit. Picton has access to the Millennium Trail, a 49 km stretch of trails that weave through County farmer’s lands, forests, creeks and marshes….perfect for hiking, biking or a fresh-air run. Or pack a picnic and head to Picton’s harbour and marina.

The Urban Part

Frugal & Co Picton PEC

Main Street Picton is lined with art galleries, clothing boutiques, foodie destinations (check out the Agrarian Market) and shops filled with home decor and vintage finds (must visit: Frugal & Company).

Picton is quickly becoming a foodie destination, with some of the area’s best restaurants, cafes, pubs and live music venues. Among our favourites: Blumen Garden, the Waring House, the County Canteen and the Acoustic Grill. See below for a complete list of our favourite restaurants in Picton.

Picton is ground zero for the County’s burgeoning craft beer scene and home to Barley Days, the County Canteen, 555, Prince Eddy’s and Parson’s Brewery, just outside of town.

Picton is also home to a thriving arts scene, with everything from a modern art gallery to rustic barn studios to local artisans selling hand-crafted products. The Arts Trail (a self-guided journey through the County’s galleries and studios) passes through Picton, with official stops at the Ungallery, Small Pond Arts and Mad Dog Arts.

The Regent Theatre, on Main Street, has been entertaining audiences since the 1920’s. With almost 450 seats, it’s the place to go to catch a movie or live entertainment, or take in the PEC Jazz Festival in August and the Classic Music Festival in September.

Other live music options in Picton: the Acoustic Grill, the County Canteen and the Barley Room at the Waring House Inn.

More urban cred? County residents regularly make the trek to Picton to shop in the area’s best grocery stores (Sobey’s, Metro and a No Frills), the big LCBO, the Beer Store, the Canadian Tire and a Home Hardware…and there are some fast food restaurants too, including a Tim Hortons.

Real Estate in Picton

Picton is a mix of heritage homes, wartime houses, condo townhouses and newly built homes. With manicured lawns and gardens throughout the town streets, buyers can choose from both renovated homes and those that need some TLC.

Lots in Picton are a good size, with typical frontages from 35-80 feet and depths typically around 120 feet. While most homes in Picton sell in the $300K – $450K range, there are options available in the low 200’s up to $750K.

There are lots of retirees in Picton, and it’s a popular landing spot for many of the young people who grew up in the County. As the cultural hub of the County, Picton is home to an educated population who enjoys the finer things in life. The town of Picton provides residents with full city services and amenities, including municipal water, sewers, roads and schools…so if you don’t want to have to worry about water wells and septic systems, Picton might be a good option for you.

Real Estate Developments of Note:

We love the condo-townhomes on the harbour/marina. Though they don’t come up for sale very often, they offer 2-4 bedrooms, outdoor terraces, water views and low condo fees (compared to Toronto). Priced in the mid 300’s to 600’s.

There’s also a small development of newer 3-storey townhouses just off of Main street, each with a private elevator, priced in the high-500’s.

Macaulay Village is an interesting subdivision near the Macauley Conversation Area, just 3 minutes from downtown Picton. With 232 freehold homes and empty lots and full municipal services, prices start in the low 200’s. You can find out more about Macaulay Village here.

The Wellings of Picton retirement community has 88 apartments for lease, for adults 55+, with a variety of a la carte services and an 8,000 sqft atrium that serves as the social hub of the community.

Must See and Do in Picton

  • Shop on Main Street Picton
  • Take a pontoon tour of the Picton marina
  • Visit the Crystal Palace (circa 1890, it’s home to many of Picton’s festivals)
  • Get a massage at the Claramount spa
  • Check out Birdhouse city
  • Take a walk through the trails at Macaulay mountain
  • People watch with a beer on a main street patio like the one at 555 Brewing Co

Our Favourite Picton Restaurants, Cafes and Pubs

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