βChristmas in the countryβ - I just love the sound of that. It makes me think of the English countryside and Rosehill cottage in The Holiday.
While I write this, am I listening to The Holiday original motion picture soundtrack? You betcha.
Back in November, I was itching for a little getaway. SO naturally, instead of reflecting on why I feel this incessant need to plan trips and zip away on outings, I planned a trip for said outing.
The vibes: a cozy couples Christmas countryside county weekend.









Hereβs what my husband and our other couple friend did during the weekend!
Check out my map of favourites and recommended spots at the end!
enjoy your outing!
π΅ Spotify playlist for the weekend: A Very Nancy Meyers Christmas
Stay
Demilune Lodge | Milford β cozy wood lodge with hints of modern design, tucked away from the town of Picton.
What a sweet airbnb! Demilune lodge was perfect for the weekend vibes. It was cozy, comfortable, and homey. It had a very well-equipped kitchen for cooking meals, board games, candles, blankets, wine glasses β all the accessories needed!






Two bedrooms and a sofa-bed room upstairs, with kitchen, living space, dining room and patio downstairs. The wood-barrel hot tub was so cute!



The lodge is on a sizeable piece of land that backs out onto the water. Itβs a 15-minute drive from Picton, perfect for what we wanted to do. This part of the County feels unpretentious to me, with original farms and small cottage homes dotting the fields.



Activities
The Eddie Red Barn Holiday Market | Bloomfield β a holiday market in the picturesque red barn, filled with local vendors, mulled wine, and hot foods. Runs one weekend only.
Wine tasting at Karlo Estates | Wellington β old-world style wines, made in traditional methods. Cozy barn with a speakeasy lounge. Vegan / plant-based snack menu. Highly recommend a reservation.
Scrabble and board games night at airbnb β ate cheese, sliced meats, drank wine, listened to Nancy Meyers Christmas playlist.
Bopping around Main Street Picton β visited cute stores with books, pottery, Christmas knick-knacks, clothing, art.
The holiday market was so cute! We headed there Saturday afternoon. Vendors were placed in a few different spots around the grounds: the greenhouse, the main barn, and then the basement of the barn (I think). It was hopping! We grabbed mulled wine (8/10) and walked the whole market. Outdoor fires were smoking outside, adding a cozy country ambiance. Inside, the barn was packed with vendors. We picked up some specialty candles, chocolates, cocktail syrup, and plushy toys.






Next stop: Karlo Estates. It was very Christmasy feeling - I loved it! I highly recommend making a reservation in the colder months though, as space is limited to areas with heating. Our server was a hoot. The other gal in our party is vegan, so it was awesome that we could pick food from an entirely vegan / plant-based menu! The wine was fine - Iβve had more enjoyable tastings at other wineries and vineyards in the County, but overall, the experience was great.



Other ideas I scoped out and put on my list, but ran out of time:
Wine tasting at Grange of Prince Edward | Wellington β a winery with its own vineyards. had a very cozy-looking stone fireplace in their tasting area that looked like such a vibe.
Beer and tacos at Slake Brewing | Milford β cool-looking brewery with a fun selection of brews. killer views from their space. plus, tacos!
Eats
Bocado | Picton β stylish Spanish restaurant on Main Street, offering up tapas, snacks plates, paella and very creative desserts.
PECish Baking Co | Milford β hip bakery with a small but mighty selection of crafted pastries, sourdough loaves, and baguettes. A bit pricey - 3 pastries for $27.
This trip was lighter on the meals out. Often, for trips with friends, I like to have a balance of meals made at home (or at airbnb) and meals out. We did two brunches and one dinner at the airbnb, with one dinner and snacks out.




Key lesson - need another day to get more time to eat!!
Loved our meal at Bocado. We had a reservation for 8pm and actually had to wait - it was the place to be on a Friday night!






We ordered from the tapas del bar section of the menu and got: croquetas de jamon, dΓ‘tiles (manchego stuffed dates wrapped in pancetta, drizzled with honey), calamares (crispy calamari with lemon aioli), patatas bravas. Delicious. Dessert was the helado del dia - which was sourdough ice cream, salted caramel drizzle and a fresh waffle cone garnish. Amazing.
What a fun weekend! I enjoy experiencing spots in Ontario in their βoffβ season, as sometimes, summer weekends are too busy or expensive. My only wish was we had an extra day to visit more spots on my list.
Till next time!