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Eight Great Towns, One Great Lake
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  • Harbor Country Chamber of Commerce
  • 15311 Three Oaks Rd
  • Three Oaks, MI 49128
  • 269-469-5409

Lakeside

Village of Lakeside, Michigan 49116

Photo by R. Quackenbush

Lakeside, like its Harbor Country sister towns, is a vacation destination and a popular choice for weddings at the historic Lakeside Inn. An active homeowners’ association sponsors several events during the year and fosters a strong sense of community. Many of the area’s leading interior design firms are located in Lakeside. An active homeowners’ association sponsors several events during the year and fosters a strong sense of community.

Helpful Links

Lakeside is governed by Chikaming Township

River Valley School District

The Lakeside Association

History

Soon after Wessel Whittaker founded New Buffalo, newly arriving pioneers must have thought the village was a bit congested. Perhaps they simply wanted less expensive land. Whatever the reason, the area’s expansion moved north across the Galien River to what is now Lakeside. An original settler named the new community “Chikaming” an Indian word meaning “at the shore of the sea.” As with other towns developing at the time, one of the first orders of business was to establish a sawmill. But it wasn’t until the 1850’s and the arrival of the Wilkinson family when real progress began. The Wilkinson’s bought 2500 acres of land along the lakeshore.

They focused their energies on the area that is now the intersection of Lakeshore Road and Pier Street. A trading post, boarding house and assorted other enterprises were established. But the jewel of the village naturally called Wilkinson was a 600-foot pier. The Wilkinson family’s schooner, the Enterprise, took lumber and bricks to Chicago and returned with supplies for the now thriving post. Wilkinson was renamed Lakeside in 1874 for reasons that remain unclear. At about that time most of the woodlands along the lake had been cleared and residents began a gripe that continues today. John Wilkinson complained that he couldn’t afford the taxes on his land. The taxes were $6.00 [Yes… Six Dollars].

The early visitors were often administrators and faculty members from the University of Chicago. In the 1920’s the Chikaming Country Club was established. A replica of Shakespeare’s birthplace was dismantled in Chicago and transported to Lakeside where it became the Chikaming Country Club’s Shakespeare House. As Lakeside was developing, and the current Red Arrow Highway was constructed, the original Wilkinson Trading Post was moved from its lake location to its current home on Red Arrow where it was eventually restored by Wilkinson heirs, Nadra and Al Kissman. Wilkinson Village houses an interesting museum, which traces the history of Lakeside. The Lakeside Inn is probably the village’s most historically romantic site. Movie stars were wined and dined there, and during Prohibition, the tale goes; Al Capone along with a variety of Chicago politicians used the Inn as a favorite drinking and gambling spot.

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15235 Lakeshore Rd
Lakeside, MI 49116 US

Phone: (269) 469-0600
E-Mail Address: manager@lakesideinns.com
Region: Lakeside

Turn of the century home in an area great for walks, close to antique shops, galleries, wineries,
More Info

15251 Lakeshore Rd
Lakeside, MI 49116 US

Phone: (269) 469-0600
E-Mail Address: reservationslk@Lakesideinns.com
Region: Lakeside
Website

A 31 room rustic hotel located across from our private Lake Michigan beach. Complete with ballroom, gran
More Info

15060 1st Rd
Lakeside, MI 49116 US

Phone: (773) 814-4467
E-Mail Address: jrmcgarry4@gmail.com
Region: Lakeside

Cottage vacation rental for relaxing by private association beach. Comfortable for small family to enjoy.
More Info

9178 Kruse Rd
Lakeside, MI 49116 US

Phone: (312) 399-1532
E-Mail Address: paintedporchcottage@yahoo.com
Region: Lakeside
Website

The Painted Porch Cottage in Lakeside, Michigan is a garden style cottage just steps away from a private, sandy beach
More Info

14634 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 469-4620
1 (800) 967-2224
E-Mail Address: info@whiterabbitinn.com
Region: Lakeside
Website

Romantic couples retreat. 2 blocks from beach. 6 rooms with whirlpools, fireplaces plus two deluxe knott
More Info

15460 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 469-1141
E-Mail Address: contact@burnisongalleries.com
Region: Lakeside
Website

Showcasing works from all artistic disciplines including 19th, 20th and 21st century classic and contemporary.Our Great ...
More Info

14876 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 469-4467
E-Mail Address: alannimmer@comcast.net
Region: Lakeside

Two large buildings with thirty-four great dealers, highest quality in the area, large assortment of oriental rugs, kilims, lighting, art, mohogany, cherry, and pine furniture from the nineteenth...
More Info

15029 Lakeside Rd
Lakeside, MI 49116 US

Phone: (269) 469-5141
E-Mail Address: chikamingcc1@csinet.net
Region: Lakeside
Website

Private Golf Club.
More Info

Lakeside, MI 49116 US

Phone: (269) 469-4859
E-Mail Address: ftomecek@earthlink.net
Region: Lakeside
Website

The Lakeside Association is a local community organization that sponsors many family events, awards grants to co
More Info

15300 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 469-2090
Region: Lakeside

Located in a former trading post built by John Wesley Wilkinson, the founder of Lakeside. This museum features artifacts ...
More Info

15310 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 469-5551
(269) 420-3811
E-Mail Address: showroom@hearthwoods.com
Region: Lakeside
Website

We work with you to create the perfect piece for your home whether it be contemporary, rustic or cottage style.
More Info

15412 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 231-5434
E-Mail Address: lakeinteriors@gmail.com
Region: Lakeside
Website

Our design service specializes in each individual project, creating custom window treatments, bedding, upholste
More Info

15412 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 612-0888
(269) 612-0290
E-Mail Address: info@whlnineyrds.com
Region: Lakeside
Website

From start to finish, we help you select window treatments - blinds and drapes. In-home consultations.
More Info

14866 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 469-0447
E-Mail Address: abigailhechejewels@gmail.com
Region: Lakeside
Website

Jewelry-- sophisticated yet simple hand worked pieces crafted from the finest materials create timeless appeal.
More Info

14939 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (269) 231-5432
E-Mail Address: info@flagship-foods.com
Region: Lakeside
Website

Welcome Aboard! Featuring delicious, fresh cooked meals ready to serve. Fresh seafood all year.
More Info

15300 Red Arrow Hwy
Lakeside, MI 49116 US

Phone: (773) 230-2640
Region: Lakeside
Website

Women's Lifestyle Clothing
More Info

15488 Lakeshore Rd.
Lakeside, MI 49116 US

Phone: (517) 617-2789
(517) 238-5368
E-Mail Address: mariadonner@msn.com
Region: Lakeside
Website

Wake up to gorgeous views of Lake Michigan and let the sound of the waves lull you to sleep.
More Info

List of Members

Members found: 17

showing 1 through 17 of 17

A Little Bit O' Heaven

15060 1st Rd
Lakeside, MI 49116
United States
Phone: (773) 814-4467
Region: Lakeside
Cottage vacation rental for relaxing by private association beach. Comfortable for small family to enjoy. More

Abigail Heche

14866 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 469-0447
Region: Lakeside
Jewelry-- sophisticated yet simple hand worked pieces crafted from the finest materials create timeless appeal. More

Burnison Galleries, Fine and Decorative Arts

15460 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 469-1141
Region: Lakeside
Showcasing works from all artistic disciplines including 19th, 20th and 21st century classic and contemporary.Our Great ... More

Chikaming Country Club

15029 Lakeside Rd
Lakeside, MI 49116
United States
Phone: (269) 469-5141
Region: Lakeside
Private Golf Club. More

Donner Thunderdune Cottage

15488 Lakeshore Rd.
Lakeside, MI 49116
United States
Phone: (517) 617-2789
Region: Lakeside
Wake up to gorgeous views of Lake Michigan and let the sound of the waves lull you to sleep. More

Flagship Specialty Foods & Fish Market

14939 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 231-5432
Region: Lakeside
Welcome Aboard! Featuring delicious, fresh cooked meals ready to serve. Fresh seafood all year. More

Hearthwoods Custom Furnishings

15310 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 469-5551
Region: Lakeside
We work with you to create the perfect piece for your home whether it be contemporary, rustic or cottage style. More

House of 11 Gables

15235 Lakeshore Rd
Lakeside, MI 49116
United States
Phone: (269) 469-0600
Region: Lakeside
Turn of the century home in an area great for walks, close to antique shops, galleries, wineries, More

Lake Interiors Inc.

15412 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 231-5434
Region: Lakeside
Our design service specializes in each individual project, creating custom window treatments, bedding, upholste More

Lakeside Antiques

14876 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 469-4467
Region: Lakeside
Two large buildings with thirty-four great dealers, highest quality in the area, large assortment of oriental rugs, kilims, lighting, art, mohogany, cherry, and pine furniture from the nineteenth century to ... More

Lakeside Association, The

Lakeside, MI 49116
United States
Phone: (269) 469-4859
Region: Lakeside
The Lakeside Association is a local community organization that sponsors many family events, awards grants to co More

Lakeside Inn

15251 Lakeshore Rd
Lakeside, MI 49116
United States
Phone: (269) 469-0600
Region: Lakeside
A 31 room rustic hotel located across from our private Lake Michigan beach. Complete with ballroom, gran More

Painted Porch Cottage

9178 Kruse Rd
Lakeside, MI 49116
United States
Phone: (312) 399-1532
Region: Lakeside
The Painted Porch Cottage in Lakeside, Michigan is a garden style cottage just steps away from a private, sandy beach More

tyler boe

15300 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (773) 230-2640
Region: Lakeside
Women's Lifestyle Clothing More

White Rabbit Inn B&B

14634 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 469-4620
Region: Lakeside
Romantic couples retreat. 2 blocks from beach. 6 rooms with whirlpools, fireplaces plus two deluxe knott More

Whole Nine Yards

15412 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 612-0888
Region: Lakeside
From start to finish, we help you select window treatments - blinds and drapes. In-home consultations. More

Wilkinson Heritage Museum

15300 Red Arrow Hwy
Lakeside, MI 49116
United States
Phone: (269) 469-2090
Region: Lakeside
Located in a former trading post built by John Wesley Wilkinson, the founder of Lakeside. This museum features artifacts ... More

showing 1 through 17 of 17