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The Merrill House in Picton, Ont., is a delightful Gothic Revival gingerbread abode that was built in 1878.

Daniel Vaughan/vaughangroup.ca/Handout

I want to visit a snow-globe-pretty kind of town to kick-start my holidays, and it can’t be too far from the GTA. Any suggestions?

Yes – put Picton in your GPS.

That’s in Prince Edward County, right?

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It is! Super charming and replete with the storybook quaintness you desire, the tiny town (home to to just under 5,000 people) boasts many establishments that are completely in sync with the sophistication of a big city.

That’s cool, but I’m really craving that cozy Whoville feel – minus the Grinch, of course.

Then you are in luck! In fact, if you just stuck to Picton’s Main Street, you’d be in holiday heaven.

Really?

Really. It’s beautiful this time of year with lots of decorations and lights, plus the Holly Jolly Holiday Market is on in the town’s Armoury. The market is a must if you’re travelling with little ones – Santa makes an appearance every Saturday and poses for pics – or even if you’re just looking for some original gift ideas. Expect to see lots of local vendors with cool merch.

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Excellent, I love shopping local. Are there any smaller independent stores I should check out as well?

Pretty much every establishment on Main Street is independently owned. If you’re a vintage fiend, you’ll be spoiled for choice: Try City Revival for clothing (take your time and look closely – Gucci items have been sourced here); and Second Time Around for overall thrifting. And – feel-good factor – they’re all great sources for sustainable gift giving. If you’re in the market for original art, Maison Depoivre and Andara Gallery showcase thoughtfully curated picks of area talent (stop by Andara just to see its showstopper Christmas tree). Bibliophiles won’t want to miss Books & Company. It has a smart edit of new releases and used books, plus it’s next door to Lily’s Café, where organic coffee is poured and homemade soups, sandwiches and treats abound. The sconces are crumbly heaven.

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What if I want to grab a pint? Any options on Main?

The County Canteen has 26 Ontario craft beers on tap. It is super casual with a pub vibe and crowd-pleasing menu: You can’t go wrong with the crispy fish tacos or the vegan coconut Thai green curry and a beer-garita (a delicious take on the traditional margarita). There’s also 555 Brewing Co, which brews its own. The IPA pairs perfectly with an in-house wood-fired pizza.

Great. Other than holiday shopping, is there anything else that’s specifically festive?

Google the listings for the Regent Theatre, a remarkable preserved Edwardian opera house that has pride of place on Main Street. Upcoming events range from holiday movies (Last Christmas) and music (A Swingin’ Christmas) to The Nutcracker presented by the County School of Dance. Picton is extremely house proud, so make time to stroll away from Main Street and spy the many significant residences decked out in all their holiday finery. Even better, this Sunday (Dec. 8), is the County House Tour. It’s self-guided and features 10 historic homes, including an 1875-built, triple-gabled farmhouse that’s set down a lane lined with century-old maples. The trees were planted to trap snow and make it easier for sleighs to navigate the lane. It will make you want to move to the country (or the county!).

I love that everything is within a few-blocks radius.

Yes, but do venture to the outskirts of Picton and treat yourself to Birdhouse City. It’s not holiday-centric necessarily, but a quirky, must-see park with more than 100 birdhouses that are replicas of well-known county buildings. The birdwatching is actually quite good, too, and has the most soothing, stress-relieving effect.

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Speaking of stress relief, I don’t want to lose that vibe by hitting the highway right away. Where should I stay for the night?

Check into Merrill House, a delightful Gothic Revival gingerbread abode that was built in 1878 for the first magistrate of Prince Edward County. Its impressive heritage has been given a contemporary revamp by owner and creative director Jordan Paul Martin. The effect is deeply comforting and cozy with all mod cons, including an outdoor barrel sauna, pillow scenting and a virtual-reality lounge. Open the front door and experience the most divine olfactory overload: The fresh, green sharpness of the real pine-bough garlands that drape the staircase, the aromatic woodsmoke of the lounge’s crackling fire and the sweet richness of a welcome mug of hot chocolate. Book “the Dreaming Suite.” It’s a bit of a splurge, yet has its own wood-burning fireplace (cocooning is very much encouraged here) and feels more Downton Abbey than downtown hotel.

All stays include a complimentary breakfast that starts with fresh fruit and warm pastries followed by temptations such as blueberry buttermilk pancakes or smoked-salmon-slathered English muffins. At night, Merrill House’s Burgundian fare restaurant, which features a swish glassed-in conservatory, is serious. In fact, it’s the only restaurant between Toronto and Ottawa with a Wine Spectator Award of Excellence. Holiday packages are available and they make this very special spot that much more enticing.

Wow – sounds like I’ll be both relaxed and raring to go for the holiday.

Exactly. So before you head back, take a slight detour and stop at Denmar Farms in Belleville, just 10 minutes north of the 401. It’s the most magical estate with more than 60,000 balsam, Fraser fir and blue spruce trees. Cut down your favourite and staff will shake it out, bundle it up and put it on your car so you can be on your – truly – merry way.

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Editor’s note: (Nov. 4, 2019) An earlier version of this story referred to the shop Frugal & Company, which has closed. This version has been updated.

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