Four-Day Winter Itinerary

With two days you could focus and explore one of our area communities but with FOUR… you could explore several. Yes, we are home to some of the best skiing and riding in northern Michigan but there really is so much more. There are wineries in the region, cultural experiences (art, museums, performances), cross country ski, snowshoe, sledding, ice skating, and more.

Want to ski your trip away? Be our guest! Check out the area ski resorts, here.

Itinerary Overview

  1. DAY 1
    1. Northwoods Restaurant
    2. Winter Rafting
    3. City Park Grill
  2. DAY 2
    1. Small Batch at the Cupola – breakfast
    2. Nordic Trails & Rental Gear
    3. Roast & Toast – Lunch
    4. Crooked Tree Arts Center
    5. Beards Brewery – Dinner
    6. High Five Spirits & Malted Vinyl
  3. DAY 3
    1. Café Sante – Breakfast
    2. Avalanche Mountain
    3. Wineries & Lunch
    4. Noggin Room Pub – Dinner
    5. Ernesto’s – Nightcap
  4. DAY 4
    1. W. Filmore’s – Breakfast
    2. Walk the Bear River
    3. Deli sandwich – Lunch

Where to Stay?

Depending on what you’re looking for in accommodation you’ll want to pick a great base location to explore every area. Check out our lodging page on our website for a full list, and check out the map view to pick something in a location you prefer.

Try Crooked River Lodge in Alanson for an outdoorsy lodge-look off the beaten path but not quite far from all things winter fun.



In between Petoskey and nearby village Alanson, you will come across Northwood Family Restaurant. Great home cooking, great portions at a good price.


Looking for something with a little adventure? Check out Big Bear Adventure in Indian River for a guided winter rafting experience. It’s truly a unique experience that you will not regret.


Drive to Downtown Petoskey to dine at City Park Grill. This restaurant is rich in history from stories of Hemingway (check out the plaque affixed to the outside of the building) to the prohibition era. This place is also not short on great food options.


  • Wedge Salad
  • Classic or their Award-Winning Chicago Burger
  • Parmesan-Herb Whitefish



To Harbor Springs for breakfast, we go! Small Batch at the Cupola in Harbor Springs serves up some seriously great breakfast and brunch dishes. Their menu is somewhat rotating but here are some menu highlights we would rave about:

  • Benedicts Garden: eggs benedict with a slight twist – rosemary ham, poached eggs, ciabatta toast, Florentine sauce, and veggies
  • King Kong: stuffed bananas foster French toast with bourbon caramel sauce & gelato
  • Lox Smith: potato pancakes, herb boursin cheese scramble eggs, smoked salmon, on mixed greens
  • Brunch Recommend: Thigh Master – crispy chicken thigh sandwich with a sriracha aioli that brings it all together


Everyone says try cross-country skiing or snowshoeing but we’re REALLY saying it. We have some magical trails that (in the right conditions) can be so much fun and give you some Instagram-worthy views to enjoy.

Great trails to check out – with plowed parking areas:

Wait, need to rent gear? Try these places:


Once you’ve worked up a hunger from exploring winter trails I am sure you’re ready for a warm bowl of soup. Check out Roast & Toast in Downtown Petoskey for usually about three or four soups to choose from! Menu highlights to try: Caesar Salad with Chicken, Avocado BLT Sandwich, or try a Sandwich/Salad & Soup Combo.


If you’re looking for something to do before dinner, check out Petoskey’s Crooked Tree Art Center (Tuesday through Saturday). The art center was originally constructed in 1890 as a church but now houses beautiful exhibits and galleries. Gallery admission is free.


Check out Beards Brewery for some great pizza or other yummy food. This casual atmosphere is the perfect spot to cozy up during the cold weather and maybe even grab a pint of Beards Brew.


Downtown Petoskey there are several places that stay open a bit later for a drink to cap your night. High Five Spirits, makers of Gypsy Vodka, Petoskey Stone Gin, and other spirits, have a tasting room downtown with a menu of specialty cocktails and offer free tiny samples of their product. Malted Vinyl, a new (and first-ever) listening lounge downtown, offers cocktails and draft beer/cider. This is just around the corner from High Five so it’s great little spot to make this night a double-feature kind of night.



Take a short drive over to Boyne City just south of Petoskey to experience European-inspired food at Café Sante. Menu highlights are Croque Madame, Vienna Pancakes, and Eggs Benedict.

Not looking to drive to Boyne City? Check out H.O. Rose Room at Stafford’s Perry Hotel for a great brunch option.


After breakfast in Boyne City head over to Avalanche Mountain Preserve to do a little winter hike or walk. Depending on conditions you may want to consider renting a pair of snowshoes or wearing cleats over your shoes.


Head towards Petoskey and stop by some wineries along the way. Mackinaw Trail Winery, Resort Pike Cidery & Winery, and Walloon Lake Winery are a few on the way to Petoskey from Boyne City to stop at. Then head over to Petoskey Farms Winery and Maple Moon Winery off of Atkins Road. For a full list of wineries check out them HERE.

Lunch AND a winery? Drive over to Pond Hill Farm in Harbor Springs for a bite at the café and try a flight of wine, cider, and beer. Highlights from Pond Hill Farm’s menu are a wood-fired pizza (Pesto Pizza, Fun Guy Pizza, or classic pepperoni to name a few), Parmesan crusted grilled cheese, and spicy peanut noodles – using their homemade Peanut Sauce & Thai Noodle Sauce.

After lunch walk around the property a bit and check out the sledding hill, trails, playground, animals, and more.


How about dinner in the basement of the Historic Stafford’s Perry Hotel? The Noggin Room Pub is a great little spot for pizza but also Fish & Chips, quesadillas, tacos, and lots of yummy appetizers to choose from. Don’t forget to grab a pint of one of their Michigan craft beer offerings.


Looking for a laid-back Cigar Lounge with a top-tier cocktail? Check out Ernesto’s Cigar Lounge in Downtown Petoskey.


For your last full day in the area you might not want to go too crazy, you have been busy!


If you’ve been thinking, “What about a hometown diner with great portions?” You’ll want to check out J.W. Filmore’s in Petoskey. Great portions and breakfast is served all day, at a decent price too! Menu highlights: one of their skillets, J.W. Breakfast, a breakfast combo, or some of their massive pancakes.


Walk by the Bear River in the Recreation Area in Downtown Petoskey. This is an easy paved trail that has views of the river from the path, viewing platforms, and as you cross over small bridges.


Depending on how far your drive is you may want to stay for lunch too. A quick meal to-go from a local deli might be the ticket from Gurney’s Bottle Shop, Toski Sands, or Cormack’s.

If you’d like to sit down and eat maybe check out Julienne Tomatoes for some great home cooking maybe even grab a dessert from their dessert case at check out that is always packed with cookies and other irresistible sweets. Menu highlights at Julienne’s are Howard Street Grill – this grilled cheese pairs well with the soup of the day fingers crossed for Tomato Gorgonzola or another tomato variety of soup, B.L. Tomato - how can you not get something with tomato when you visit, California Turkey Club, or Robyn’s Reuben. So many great choices, salads too!

We hope you had a fantastic trip!