Each year, Old Rittenhouse Inn and Bayfield, Wisconsin, host many Special Events. These events create even more reasons to visit the “Best Little Town in the Midwest” at any time of year. See what’s coming up below.

August, 2020
Day(s) Date(s) Event
Sat August 1, 2020 Point to LaPointe Swim Race

This annual swim race from Bayfield to Madeline Island consistently sells out its 550 spots. Support personnel accompany swimmers by kayak. Event Web Page

Tue August 4, 11, 18, 25, 2020 Concerts By The Lake

Bayfield’s Concerts By The Lake take place from mid-June to early September at Memorial Park featuring popular local and regional musicians. The Tuesday night shows are free and open to the public. Event Web Page

Show time is 7 – 9pm. 

September, 2020
Day(s) Date(s) Event
Tue September 1, 8, 2020 Concerts By The Lake

Bayfield’s Concerts By The Lake take place from mid-June to early September at Memorial Park featuring popular local and regional musicians. The Tuesday night shows are free and open to the public. Event Web Page

Show time is 7 – 9pm. 

October, 2020
Day(s) Date(s) Event
Fri - Sun October 2 - 4, 2020 Apple Festival

Named one of the Ten Best Fall Harvest Festivals in the Nation by USA today, Bayfield’s Apple Fest is now in its 56th year. Make your lodging plans well ahead of time, as the average attendance is over 50,000. Bayfield Apple Festival Web Site

Sat October 10, 2020 Whistlestop Marathon, Blues & Brews

Nearby Ashland’s premier fall event combines a marathon and half marathon with a blues festival and beer tasting. The marathon course is relatively flat and well paved, winding its way through lush woods full of gorgeous fall color. Event Web Page

November, 2020
Day(s) Date(s) Event
Wed - Sat November 4 - 7, 2020 Big Water Film Festival

Featuring films by local and regional artists, as well as national and international releases, the Big Water Film Festival is held at nearby Ashland WI’s Bay Theater with additional screenings in Bayfield, Washburn and Drummond, WI. Event Web Site

Fri & Sat November 6, 7, 2020 Fall Brew Weekend

Sample a wide variety of local, regional, and imported brews at this entire weekend dedicated to great beer, food, and friends. Meet the brewers, take a tour, and try the many styles including Pilsners, Lagers, Pale Ales, ‘Fest’ Beers, Porters, and more.

Fri & Sat November 13, 14, 2020 Red Wine Weekend

Sample and enjoy a variety of Cabernets, Zinfandels, Merlots, and Pinot Noirs and more at this weekend dedicated to great wine, food, and friends.

Wed - Fri November 25 - 27, 2020 Thanksgiving at the Inn

Landmark Restaurant at Old Rittenhouse Inn is open for Thanksgiving Dinner from 1:00pm to 7:00pm. We will offer a special 2-night Thanksgiving Lodging and Dining Package, available Wednesday through Friday.

Fri - Mon November 28 - 30, 2020 Shop Hop Passport

Experience the best of holiday shopping at Bayfield’s Holiday Shop Hop. Enjoy great deals and holiday prizes all while supporting local businesses! Learn More

Sat November 28, 2020 Holiday Tree Lighting Ceremony

Come usher in the holiday on one of Bayfield’s magical winter nights. Enjoy treats, warm drinks, and Christmas carols! Read More.

Join us between 4:30 and 6pm on Saturday, November 28th.

Sat November 28, 2020 Madeline Island Holiday Boutique

Visit the Madeline Island Museum and browse an enticing variety of hand-crafted arts and goods for sale at this beloved traditional holiday event featuring local and regional arts and crafts.

Sat & Sun November 28, 29, 2020 Wassail Concert

11/28 6:30PM Wassail Concert
11/29 12:00PM Wassail Concert

People of all ages will enjoy this event combining a gourmet meal with holiday chamber music by the Old Rittenhouse Singers. Our 1890s Queen Anne Victorian Mansion is decorated for the season with pine bough roping and twinkling white lights, with a gigantic 16′ Christmas tree decorated with hundreds of ornaments. More Info

December, 2020
Day(s) Date(s) Event
Tue December 1, 2020 Bayfield Hometown Holidays

Bayfield is a special place to spend the holiday season. In addition to our Wassail Concerts at Old Rittenhouse Inn, there is much to see and do in our town including holiday shopping, celebrating with friends, or taking advantage of Bayfield’s wealth of outdoor activities. The scheduled events include the Holiday Shop Hop, the Holiday Tree Lighting Ceremony, Bayfield’s Shop Local for the Holidays Night, the Holiday Spirit Gallery Tour and, of course, Santa’s Arrival on the Madeline Island Ferry! Event Web Page

Tue - Mon December 1 - 14, 2020 Shop Hop Passport

Experience the best of holiday shopping at Bayfield’s Holiday Shop Hop. Enjoy great deals and holiday prizes all while supporting local businesses! Learn More

Thur - Sun December 3 - 6, 2020 Wassail Concert

12/3 6:30PM Wassail Concert
12/4 12:00PM Wassail Concert
12/5 12:00PM Wassail Concert
12/5 6:30PM Wassail Concert
12/6 12:00PM Wassail Concert

People of all ages will enjoy this event combining a gourmet meal with holiday chamber music by the Old Rittenhouse Singers. Our 1890s Queen Anne Victorian Mansion is decorated for the season with pine bough roping and twinkling white lights, with a gigantic 16′ Christmas tree decorated with hundreds of ornaments. More Info

Fri December 4, 2020 Bayfield's Shop Local for the Holidays Night

Celebrate the holidays with special sales and late hours at our local businesses! Learn More

Event hours are from 5 – 8pm. 

Sat December 5, 2020 Holiday Spirit Gallery Tour

Come experience the best of Bayfield’s galleries with local tours featuring handmade jewelry, pottery, paintings, and more! You’ll find something for everyone on your gift list. Read more.

Explore the galleries from 10am – 5pm on Saturday, December 5th.

Sat December 12, 2020 Santa Arrives on the Ferry

Bring the kids for pictures with Santa Claus as he rides into town on the Madeline Island Ferry! Read More

Come meet Santa from 11:30am – 1pm on Saturday, December 12th.

Sat & Sun December 12, 13, 2020 Wassail Concert

12/12 12:00PM Wassail Concert
12/12 6:30PM Wassail Concert
12/13 12:00PM Wassail Concert

People of all ages will enjoy this event combining a gourmet meal with holiday chamber music by the Old Rittenhouse Singers. Our 1890s Queen Anne Victorian Mansion is decorated for the season with pine bough roping and twinkling white lights, with a gigantic 16′ Christmas tree decorated with hundreds of ornaments. More Info

Sat & Sun December 19, 20, 2020 Wassail Concert

12/19 12:00PM Wassail Concert
12/19 6:30PM Wassail Concert
12/20 12:00PM Wassail Concert
12/20 6:30PM Wassail Concert

People of all ages will enjoy this event combining a gourmet meal with holiday chamber music by the Old Rittenhouse Singers. Our 1890s Queen Anne Victorian Mansion is decorated for the season with pine bough roping and twinkling white lights, with a gigantic 16′ Christmas tree decorated with hundreds of ornaments. More Info

January, 2021
Day(s) Date(s) Event
No Events this Month
February, 2021
Day(s) Date(s) Event
Sat & Sun February 6, 7, 2021 Apostle Islands Sled Dog Race

Grab your winter gear and get ready for some fun at the 25th Annual Apostle Islands Sled Dog Race. Pick a team and follow them through the checkpoints, or find a good spot and watch all the mushers come through. Each station provides coffee and hot water to warm up, and there are a variety of other activities to enjoy throughout the weekend. AISDR Web Site

March, 2021
Day(s) Date(s) Event
No Events this Month
April, 2021
Day(s) Date(s) Event
No Events this Month
May, 2021
Day(s) Date(s) Event
No Events this Month
June, 2021
Day(s) Date(s) Event
No Events this Month
July, 2021
Day(s) Date(s) Event
No Events this Month