When winter snow blankets Southwest Michigan, the region transforms into a playground for cozy gatherings and outdoor adventures. Whether you’re planning a weekend getaway with friends, a family outing, or a team-building trip, there’s no shortage of fun to be had. From hiking or snowshoeing through quiet trails to exploring local wineries and restaurants, Southwest Michigan offers something for every group to enjoy. Here’s our list of the best winter group activities in Southwest Michigan — where chilly days turn into warm memories. Of course, The Neighborhood Hotel is the ultimate place to begin and end your days of togetherness.
1. Sled @ Warren Dunes: Choose the main dune overlooking Lake Michigan or hike inland if you want the ‘hill’ to yourself. Both locations offer great climbs, amazing views and sweet rides. Feel like snowshoeing your way through the beauty? We’ve got some for you ready and waiting!
2. Winter Hikes: As mentioned, Warren Dunes State Park is great for sledding and hikes – can’t get enough of those views. The Chikaming Township Park & Preserve is a cool spot to explore wetlands, woodlands, prairie, Galien River frontage, and an inland lake. Or, wander amongst beech maples at Warren Woods State Park.
3. Fat Tire Bikes: These bikes are wider, heavier and slower than traditional mountain bikes so they’re able to provide traction and stability on terrain that’s off-limits to bikers (things like sand and snow). Find rentals + trails at Love Creek County Park or ride your own bike on the varying skill-level trails at Chikaming Township Park & Preserve. Fat tire bikes are also a fantastic way to explore the winter lakeshore (although they’re not allowed on the beach at Warren Dunes).
4. Majestic winter sun @ the beach: Don’t miss a winter sunset – completely worth the chill and just a 5 minute walk from the hotels!
5. Winter s’mores over our fire pits!
6. Private Chef/Cocktail/Mocktail Experiences @ The Hotel! Let us know what your heart desires and we’ll connect you with the right person to make your food/bev dreams come true! Our kitchen/living room is the ultimate spot for things like this!
7. Game Nights @ The Hotel! There really is never a dull moment here. Stay active with some ping pong (at Grand Beach) or get focused over board/card games. BYOG (bring your own game) or check out our stash!
8. Igloo Experiences @ Round Barn: Bundle up, bring your blankets and truly experience a “Michigan winter” in an Igloo at Round Barn’s Winter Village. Igloos are heated (weather depending), stocked with games, food/drinks to order and lots of fun.
9. Taste of Granor Farm Dinners: Taste of Granor features crops grown on the farm & is a true celebration of the food culture in southwest Michigan. The tables are long, conversation is good. Every meal is unique to the moment in time, featuring vegetables and grains grown by Granor and other ingredients from neighboring farms.
10. WINERY & BREWERY HOP & GOOD EATS
We love…
–Shady Creek Winery: This is the go-to spot to enjoy family/friends in a place that’s beautiful with delicious wine that’s approachable.
*10 Minutes from the Hotels
–River Saint Joe: A farmstead brewery/restaurant on Flatwater Farm, a 180-acre certified organic farm w/ a lovely beer garden!
*30 Minutes from the Hotels
–Hickory Creek Winery: Hickory Creek’s iconic red barn houses their cozy tasting room. Owner/winemaker, Adam McBride, is often there welcoming guests.
*30 Minutes from the Hotels
– Round Barn Winery, Distillery and Brewery: Great place with a cool lineup of concerts and festivals May-October.
*30 Minutes from the Hotel
–Dablon Winery + Vineyard: This is a beautiful and vast vineyard that features wines crafted in the styles of Burgundy/Bordeaux.
*30 Minutes from the Hotel
–Beer Church Brewing: Housed in a former Methodist church (which is beautiful) you’ll enjoy great beer and awesome food (like wood fired pizza) inside or in the garden!
*10 Minutes from the Hotels
–PostBoy is your spot for family friendly delicious & fresh food (go healthy or calorie splurge), wine/beer/cocktails & a bumping patio scene.
*10 Minutes from each Hotel (walkable from New Buffalo)
–Farmette is the sweetest, roadside spot! It’s a small farm, marketplace, bakery + cafe — the ultimate one-stop sustainable shop featuring all the best stuff. Go for local produce, flowers, coffee, cheese, bread, wine, beer, prepared foods, home goods + more.
**10 Minutes from each Hotel.
–Cafe Farina is situated in the heart of Michigan City’s historical district and is the ultimate, cool yet cozy spot for delicious Italian food.
*20-30 Minutes from each Hotel.
–Rocco’s features more delicious dishes from the owner’s of Cafe Farina. Another great reason to checkout the vibrant area of Michigan City! Go for a great, relaxed atmosphere and tasty Italian food.
*20-30 Minutes from each Hotel.
About The Neighborhood Hotel
The Neighborhood Hotel was founded in 2020 by travel enthusiasts who enjoy spaces that inspire, comfort and fuel. Each suite is well equipped for short and longterm stays (i.e. kitchens, laundry, etc.). The Neighborhood Hotel transforms old buildings with compelling history into well outfitted apartment style hotels that honor the old while representing the now. The vibe is fresh and fun with rooms that are stocked to support everyone from the homebody to the adventurer. The hotels provide a basecamp for the explorer and a sanctuary for the traveler who needs to recharge, reset or just chill. The suites are simple and clean, punctuated with accents that bring the right amount of pop. The Neighborhood Hotel has locations in Chicago: Lincoln Park, Little Italy, West Loop (2026 opening) and Southwest Michigan: New Buffalo and Grand Beach.
Read about TNBHD in: Architectural Digest, Midwest Living and CN Traveler!
Connect with @the.neighborhood.hotel on Instagram and LinkedIn!
