Best Places to Visit During Winter in Connecticut, From Lifelong Local

This Kent Collection boutique hotel reminds me of the Dragonfly Inn from “Gilmore Girls.”

It’s a great place for an overnight stay in New England — book the vintage railcar, cozy barn-style “bunk house,” or more classic room in The Firefly Inn.

I love that so many of its spaces are complete with fireplaces, whimsical floral wallpaper, and other cozy details.

A stay at The Firefly Inn is just the luxury you’ll need after exploring Kent Falls — one of the tallest waterfalls in the state — and Bull’s Bridge, which you can use to access the Appalachian Trail.

While in the area, grab a delightful fireside bite at Fife ‘n Drum Restaurant & Inn, like its hearty house-braised corned-beef reuben or light grilled-shrimp salad.

A stay at The Litchfield Inn is perfect for a charming New England getaway. This traditional-yet-modern-farmhouse-style boutique hotel is nestled on 10 acres in the Berkshires foothills.

While in the area, grab a peppermint latte and cinnamon roll from @ The Corner. Or, drop by Espresso 59 for a chocolate-marshmallow cookie or giant chocolate-filled cupcake.

Pop into Milton Market to peruse beautiful home-decor finds and maybe even treat yourself to a new canvas tote with a leather tag.

A weekend at the Delamar Southport is a delight — especially if you choose to indulge in a balancing stone massage.

The hotel is home to the Artisan, which I’d consider to be the best upscale restaurant in Southport. It’s a great place for an intimate hangout over a fine bottle of red.

At dusk, curl up on an Adirondack chair by one of the property’s outdoor fire pits for s’mores roasting.

Terrain has a few locations throughout the US, but I’m especially fond of the one in Westport.

The garden and homeware store is also a full-service restaurant, serving seasonally inspired brunch and dinner dishes.

I love sipping a mug of hot cocoa or a toasted-marshmallow espresso martini by the fire in Terrain’s outdoor garden, surrounded by evergreen wreaths and trees (that are also available for purchase).

This darling winery is nestled in the rolling hills of Newtown.

Consider gathering a group of friends to participate in dreamy events at Aquila’s Nest, such as wreath-making or pairing gourmet chocolates with wines.

For an elevated date night, book a wine tasting in one of the property’s igloos or a luxury seasonal picnic.

Grab an Instagram-worthy wintery coffee and a goat-cheese tartine before shopping at GrayBarns’ country store along the Silvermine River.

It’s regularly home to a range of seasonal pop-ups, from flower trucks to displays from high-end fashion brands.

It’s not just a café-marketplace hybrid, either — the property is also a farmhouse-style inn with an upscale tavern where visitors can enjoy their meals by a rustic stone fireplace.

One of my go-to breakfast spots in the winter is Harborview Market.

Many locals head here for The Paisan — an omelette with prosciutto, tomato, pesto, and fresh mozzarella — and a seasonal cup of joe.

Find your own private table, or share one family-style with other diners. If the sun is shining, there’s always seating on the patio.

Check out the T-shirts, sweatshirts, and coffee beans for a fun take-home gift. Personally, I never leave Harborview without buying a box of freshly baked sea-salt chocolate-chip cookies.

Every winter morning should start with a bacon, egg, and cheese — and The Tasty Yolk delivers the goods.

The local favorite breakfast spot has several locations and food trucks in the state, though I’m partial to the one by the Fairfield/Bridgeport line.

Even on cold days, I’ve seen long lines of people waiting outside this cute little food truck just to snag a warm, oversized breakfast sandwich.

Grabbing food and doing some shopping in Greenwich is a perfect New England day trip.

Greenwich Avenue — known by locals as “The Ave” — is home to several high-end stores, like LoveShackFancy, and a slew of excellent cafés and restaurants.

I suggest grabbing an elevated brunch at The Cottage or coffee and freshly baked French pastries at Raphaël’s.

Sometimes, the best plans are the simplest ones.

Bundle up and hike to Sleeping Giant — a small mountain in Hamden that’s over 700 feet tall — for an incredible workout and views.

You can even have a cozy picnic in the state park; just be sure to pack a thermos of hot chocolate and pick up sandwiches from Meat & Co. nearby in New Haven before heading out.