Greetings, cabin cozy-seekers! Winter in the Northwoods means crisp air, sauna steams, and that unbeatable craving for comfort food after a day on the lake (or just binge-watching the snow fall from the deck). While summer brings its own seasonal spots, winter dining around Stone Lake and Hayward leans into hearty, open-year-round favorites that hit different when it's chilly out. We've rounded up our top 5 go-tos—places we (and our guests) hit again and again. These are all easy drives from our O’Connell Cabin Co. lakefront spots, perfect for a night off from the cabin kitchen... or grabbing takeout to warm up by the fireplace.
Whether you're celebrating the holidays, sneaking in a NYE toast, or just fueling up for more dock-side snow angels, these spots deliver. Let's dig in!
#1 Pine Ridge – Our All-Time Favorite Rustic Gem
Just 15 minutes from the cabins on beautiful Sissabagama Lake, Pine Ridge opens at 4 PM Thursday through Sunday—and trust me, arrive right on time to snag a table because this place fills up fast (for all the right reasons). Famous for their family-style fish fry, but honestly, everything shines. My personal obsession? The Pit Ham Alfredo—creamy, smoky perfection. And save room for the bread pudding; it's straight-up heavenly. Pro move: If cooking's not on the agenda, order entrees to-go and reheat in the cabin microwave. We do it all the time!
#2 Coop’s Pizza – Family-Friendly Cabin Vibes
20 minutes away in Hayward, Coop’s feels like an extension of your O’Connell cabin—log walls, cozy atmosphere, and food that brings everyone together. Killer pizza (homemade crust, fresh toppings), a fresh salad bar, arcade for the kids (or kids at heart), and even outdoor seating when the weather cooperates. Insider tip: Grab a frozen pizza from the freezer by the door—we swing by every time we're in town and toss one in the cabin freezer for lazy nights. You won't regret it!
#3 Angler’s Bar and Grill – Classic Up-North Heart
Smack on historic Main Street in Hayward (20-minute drive), Angler’s nails that authentic bar & grill feel—warm, welcoming, and packed with locals. Wide menu for everyone: juicy burgers, pizza, apps galore, kids' options, Friday fish fry, Saturday prime rib, even gluten-free picks. It's the spot for soaking in Hayward energy without venturing far from your quiet lakefront haven.
#4 Summers on Long – Brunch Bliss All Winter Long
Don’t let the name fool you—this gem on Long Lake stays open through the snow (20-minute drive). Fantastic menu, friendly staff that treats you like family, and brunch that's next-level good any day. Go for the Brisket Eggs Benedict—tender, flavorful, and the ultimate winter warmer. Breakfast, lunch, or dinner—you can't go wrong here.
#5 Red Schoolhouse Wines – Charming Wine Spot Right Nearby
Only 10 minutes away in Stone Lake, this converted 1870s schoolhouse is one of the coolest hangs around. Unique bar, great wines/spirits, tasty bites (flatbreads, apps), and a gift shop where you can snag that favorite bottle to enjoy back at the cabin. Perfect for a relaxed evening unwind—history, charm, and a glass in hand.
There you have it—our winter-tested lineup for turning "what's for dinner?" into "when are we going back?" These spots make skipping the cabin stove totally worth it (or grabbing takeout to enjoy lakeside). Got a favorite we missed? Let us know — we're always scouting!
Craving these flavors ASAP? A few prime winter weeks are still open (and shoulder-season steals for early 2026)—peek at oconnellcabinco.com and let's get you booked.
Pro Tip: Call ahead for Pine Ridge or Angler’s on weekends—they get hopping! And pair any meal with a post-dinner sauna session back at Cattail Chalet. Those dates are filling fast—check oconnellcabinco.com today.