Things to Do

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Seasonal Activities / Events

Dudeck’s Pine Country

through December 22, Rolling Prairie
Located on a beautiful 80-acre rolling hillside in nearby La Porte County, Dudeck's is our favorite tree farm. Horse-drawn wagon rides, Santa sightings, and a gorgeous selection of trees, wreaths and garlands.

Teddy Bear Tea

December 7, Marina Grand Resort
Our 14th annual benefit for Toys for Tots promises a magical afternoon of giving, snacking and dancing. Enjoy kid-friendly tea service and treats, chat with Santa, then get your groove on with award-winning kindie band Poochamungas! Admission is $10 per person and a donation of a new, unwrapped toy. For reservations, call 269.469.9900.

Giggle & Mingle with Santa Claus

December 6, Round Barn Winery, Baroda
A fun family event at Round Barn's beautiful estate. Kids activities include ornament making and cookie decorating, as well as photo ops with Santa. Adult activities include wine and beer tasting, and handcrafted DiVine cocktails. All set to a festive soundtrack, admission is a $5 donation to Toys for Tots, or a new, unwrapped toy.

Sawyer Garden Center Christmas Open House

December 5-7, Sawyer
Boasting 17,000 square feet of Christmas trees and holiday decor, shop this three-day event sure to jazz up your home for the season. Enjoy gourmet food and wine tastings along with raffles and product deals.

William Florian: Those Were the Days

December 6, Acorn Theater, Three Oaks
William Florian, lead singer of New Christy Minstrels, presents an upbeat journey through America’s most memorable soft rock hits from bands like Peter, Paul and Mary, John Denver and Pete Seeger.

The Nutcracker

December 6, New Buffalo Performing Arts Center
Southold Dance Theater performs the classic holiday ballet in New Buffalo's state-of-the-art performing arts center.

Corky Siegel and Howard Levy

December 12, Acorn Theater, Three Oaks
Composer and chamber blues statesman Corky Siegel teams up with Howard Levy, founding member of Bela Fleck and the Flecktones. Dynamic, playful performers, master musicians and great friends, this is sure to be a night of stellar jazz and blues improvisation.

Street Carols and Jingle Bell Rocks

December 13, Acorn Theater, Three Oaks
Improv queen Roxy Bellows hosts this holiday-themed doo-wop performance from The Spanials, Willie Rogers of the Soul Stirrers, and premier a cappella group, Stormy Weather. Following the concert is a screening of Jingle Bell Rocks, a documentary that delves into the minds of the world’s most unusual Christmas music fanatics who are reinventing the seasonal soundtrack for the 21st century.

Foiled Again

December 14, Acorn Theater, Three Oaks
Chicago cabaret trio Foiled Again returns to the Acorn stage with their lush harmonies and original renditions of holiday favorites.


December 20, Four Winds Casino, New Buffalo
Award-winning five-piece Native American rock ensemble Brulé combines theatrical instrumentals with an authentic dance troupe, giving audiences a genuine cultural experience.

Christmas at the Acorn

December 20, Acorn Theater, Three Oaks
A holiday extravaganza of top-notch vocalists leading the audience in Christmas carol sing-alongs, all accompanied by musicians on the harp, piano and Barton Organ. Holiday cocktails and treats, as well as fresh-roasted chestnuts make for an irresistible night of holiday cheer.

After Holiday Fun

December 26, Journeyman Distillery, Three Oaks
Enjoy live tunes as you sip on artisan-crafted cocktails or a spicy cure-all bloody Mary in Journeyman’s industrial-chic lounge.

Walkable New Year's Eve

December 31, Casey’s Restaurant, New Buffalo
Ring in the New Year with live music and plenty of local color at Casey’s neighborhood bar.

New Year’s Eve at Four Winds Casino

December 31, New Buffalo
Super-danceable live music from Sushi Roll, special offers and multiple cash prizes awarded throughout the evening make Four Winds the place to be for New Year's gaming and fun.

Super Happy Funtime Burlesque

December 31, Acorn Theater, Three Oaks

New Year’s burlesque is a time-honored Acorn tradition. Sexy, irreverent and above all things, fun, SHFB brings back the naughty after all the holiday nice. Cash bar and food follow the show.

Journeyman Distillery Tours

Saturdays, Three Oaks
Journeyman distillers share the history of the Featherbone Factory building as well as the step-by-step of spirit making. A tasting in the industrial-chic lounge follows the tour.

December at Acorn Theater

A turn of the century corset factory turned live performance theater, the Acorn is a Harbor Country jewel. Performances in December feature an eclectic array of live music, theater, comedy and storytelling.

December at Vickers Theatre

Three Oaks
Another turn of the century building lovingly restored into a beautiful film house and gallery. The Vickers offers a well-curated selection of independent and foreign films.

Live Music at Hard Rock Café

Four Winds Casino, New Buffalo
Regionally and nationally known bands perform nightly at Harbor Country’s newest music venue.

Four Winds Casino

New Buffalo
Gaming fans will find a Vegas-caliber casino set deep in the woods, just minutes away, at Four Winds Casino. Don't feel like driving? Enjoy complimentary shuttle service.

Southwest Michigan Wine Trail Tours

Maps are available at the Front Desk for an easy self-guided tour to our fifteen area vineyards and wineries. Or, if you prefer to explore the wine trail without having to worry about driving, private charters and hop-on tours are available through Leisure Limousine, Grape & Grain Tours, and Fruitful Vine Wine Tours.

Winter Hiking

Harbor Country offers great hiking in diverse settings. Explore Warren Dunes State Park, Chikaming Park & Preserve, Robinson Woods, Warren Woods and Galien River County Park. Or bundle up and walk for miles on New Buffalo’s beautiful public beach.

Deer Creek Hunt Club

Three Oaks
Three sporting clay courses and upland bird hunting on 500 acres of beautiful ravine woodlands, streams, rolling hills and contoured cover fields.

Shopping and Gallery Tours

Harbor Country is loaded with unique places to shop, but some of the best are located just off the beaten path. We can design individual mini-tours by town or by interest. Please inquire when making your reservation – we’ll have a list of shops, hours and directions ready for you at check-in!

Christmas at the Acorn

December 20, Acorn Theater, Three Oaks
A holiday extravaganza of top-notch vocalists leading the audience in Christmas carol sing-alongs, all accompanied by musicians on the harp, piano and Barton Organ. Holiday cocktails and treats, as well as fresh-roasted chestnuts make for an irresistible night of holiday cheer.



Bentwood Tavern

brunch, lunch and dinner

Blue Plate Café

breakfast and lunch

Brewster's Italian Cafe

lunch and dinner

Café Gulistan


Casey's Bar & Grill

lunch, dinner and drinks

David’s Delicatessen

breakfast and lunch


breakfast and lunch

Jackie’s Cafe

breakfast and lunch


lunch, dinner and drinks


coffee market, wine, beer and gourmet snacks

Luisa’s Café

breakfast and lunch

Mesa Luna

brunch and dinner

Nani's Café

breakfast and lunch

Pierre Anne Creperie

brunch and lunch

Pleasant House

lunch, dinner and drinks

Red Arrow Roadhouse

lunch and dinner


lunch and dinner

(closed for season)


breakfast and lunch


lunch and dinner

Stray Dog Bar & Grill

lunch, dinner and drinks

Tabor Hill Winery & Restaurant

lunch and dinner

Terrace Room

dinner and drinks






Captain Mike's Fun Park

(closed for season)

Hesston Steam Museum

I Love Toys & Trains

New Buffalo Township Park & Preserve

playground, splash park, basketball, bocce, volleyball, nature trails and amphitheatre

Washington Park Zoo

Outdoor Activities

Chikaming Township Park & Preserve

Deer Creek Hunt Club

Galien River County Park

New Buffalo Sailing Excursions

(closed for season)

Oselka Marina

boat and wave runner rentals

(closed for season)

Outpost Sports

bike and kayak rentals and lessons

(closed for season)

Stateline Stables

horseback riding

Steel-N-Time Charters

(closed for season)

Third Coast Surf Shop

surf and kayak rentals

(closed for season)

Warren Dunes State Park

Waya Rentals

boat rental

(closed for season)


Abigail Heche



women’s boutique

Catherine Doll

women's fashion, art and gifts

Center of the World Woodshop

handcrafted Art & Crafts furnishing

Customs Imports

home furnishings and pottery


women's boutique


garden-inspired gifts and home furnishings

French Twist

designer fashions

Go Fish

antique and vintage

Harbert Antique Mall


Hearthwoods Custom Furnishings

home furnishings

Ipso Facto

antique, vintage and unique furnishings and objects


Lakeside Antiques

antique mall


Lighthouse Place Premium Outlets


sustainable foods and cured meats

Lovell & Whyte

home furnishings

Marco Polo

antiques and vintage finds

Mix & Mingle

home furnishings and design

Outpost Sports

bike and kayak rentals and lessons

(closed for season)

Sawyer Home & Garden Center

home décor, garden supplies, gourmet goods and local produce

Season's Harvest

gourmet sauces and gifts


vintage and modern

Third Coast Surf Shop

surf clothing and gear

(closed for season)


vintage, antique, art, design

Urban Soles

men and women’s footwear and accessories


men's and women’s apparel

Whittaker House

men’s and women’s apparel

Theatres / Entertainment

Acorn Theater

live music and theater

Dunes Summer Theatre

community theater

(closed for season)

Vickers Theatre

independent film

Wine, Beer & Spirits