To fill vacancies, support local business, and maintain a vibrant place for all, Downtown Main Street offers grants to retail and restaurant entrepreneurs to attract new business in our historic downtown.

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Past Success

In 2014, Red Wing Downtown Main Street hosted a Restaurant Challenge to help fill several vacant restaurant spaces downtown. This Challenge saw winner John Flicek open Staghead Restaurant, which was a beloved establishment lasting almost ten years. In 2016, the Red Wing Downtown Main Street hosted a Retail Challenge that netted four new businesses to downtown Red Wing. We received eight initial applications, and five moved on to the final round. Andrew Petersen of Red Wing Bicycle Company was 2016's winner with Rivertown Comics & Game, Backwoods Framing & Engraving, and Red Wing Mercantile runners-up. Rivertown Comics and Games is still open seven years later.

Last year, the 2024 Challenge saw winner Michelle Tracy of Creative Hand open a “Hat Bar” which catered to experiential shoppers who created custom trucker hats. Supporting these types of experiences with viral cache are important in developing downtown as a destination with unique offerings. Other winner Karna Pettit took over Hallstrom’s Florist which is now Riverbend Floral Studio. Karna’s concept is a refresh while importantly carrying on a legacy business in the same location. She also is a next generation entrepreneur showing the Challenge’s commitment to growing local talent. Karna has been active in supporting community activities being involved with Fairy Fest and Holiday Stroll.

In the summer of 2025 we hosted another challenge and from the initial 21 applications submitted, 6 winners were awarded grants. These businesses included two existing retail spots: Rivertown Games and The Artisan Collective. Four new businesses were able to get launched with their funds. These businesses are: Ivory & Wing (a bridal boutique), Achieve Collective (a play space and cafe), Smith & Trade (local artisan made goods), and North Star Stitching Studio (a quilt shop).

Overview

Red Wing Downtown Main Street and our partners are offering incentive package(s) for retail & restaurant business opening or doing a significant expansion in Red Wing’s historic downtown. We have grants available to match up to 25% of your project.

Before starting, check out these local resources…

Red Wing Ignite

Free business assistance, education, and training.

Learn more: www.redwingignite.org

Red Wing Port Authority

Low-interest loan to qualified applicants.

Sign/awning grants available.

Learn more: www.redwingportauthority.org

Potential Available Spaces

Locations are always ch anging, email director@downtownredwing.org for curren t openings.

Summary

The Retail & Restaurant Challenge is an entrepreneurial start-up grant program designed to spur economic growth in Red Wing. Business concepts eligible for the competition include:

Significant expansion of a current downtown retail and/or restaurant business that includes an added business concept. (Current businesses applying need to be a paid Partner with Downtown Main Street in good standing.)
Brand new businesses opening in a current vacancy. Some ideas we would love to see in our downtown: ethnically diverse restaurants, footwear stores, outfitter retail shops, and experiential businesses. It is important to prioritize businesses that are open 7 days a week.

Specifics

The funds may be spent on related costs to the start up or expansion.

Cannot be used on inventory, payroll, previous purchases, rent, or membership fees.

Examples of possible uses: build out costs, POS system, remodeling costs, equipment, fixtures, etc.

Grant disbursement will be in the form of reimbursements and/or direct contractor payments. Receipts/invoices required for reimbursement.

Judging

The Judging Panel will comprise a mix of business owners, representative(s) from Downtown Philanthropic Collaborative* (DPC), economic development partners, and Red Wing Downtown Main Street Board. Judges will select those who will advance to the next phase.

*DPC is made up of local foundations including: Albrecht-Poss Family Foundation,Jones Family Foundation,Red Wi ng Area Fund, Wings Foundation.

Goals

Recruit businesses that will enhance the business mix in downtown Red Wing.
Provide businesses a head start during the most challenging year of operation (the first year).
Strengthen the local economy by attracting unique and specialty businesses.
Transform empty business spaces into more attractive and beneficial locations.
Build a “buzz” and promote Red Wing as a great place to start a business.
Display the community’s commitment to downtown Red Wing.

Timeline

The judges meet at these specific times of the year.

Applications submitted by May 1, 2026, will be reviewed by the judging panel. If your application advances to phase 2 you will pitch to the judging panel on May 18, 2026.
Applications submitted by July 1, 2026, will be reviewed by the judging panel. If your application advances to phase 2 you will pitch to the judging panel on July 13, 2026.
Applications submitted by September 1, 2026, will be reviewed by the judging panel. If your application advances to phase 2 you will pitch to the judging panel on September 21, 2026.
Applications submitted by January 1, 2027, will be reviewed by the judging panel. If your application advances to phase 2 you will pitch to the judging panel on January 11, 2027.
Applications submitted by March 1, 2027, will be reviewed by the judging panel. If your application advances to phase 2 you will pitch to the judging panel on March 8, 2027.

Contest Components

Phase 1 – Business Plan Application–Business Concept for new or existing businesses

Applicants will be required to submit an official application form. Applicants are encouraged to use creativity in the description. This application will be similar to a full business plan and it is meant to better understand your concept to assess if your application will move forward to the next phase.

The application form shall be submitted by midnight on the application window of your choosing.

*See the timeline above

Application form is located here ⬇️

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Phase 2 – Final Pitch

There will be a pitch and short dialogue with the Retail & Restaurant Challenge Judges. Participants will describe their idea in person in front of the judges. The presentation can be verbal or include media (video, PowerPoint, etc). The judges will fully examine the plans and presentations and determine the winners.

These will take place on May 13, July 18, Sept 21, 2026 and Jan 11, or Mar 8, 2027 time TBD.

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Rules and Eligibility

Eligibility

The contest is open to all legal U.S. residents 18 years of age and older at the time of entry.
Proposed businesses must be for-profit.
Proposed businesses can be independent operations or franchised.
Proposed businesses can be a one-person concept or a team concept.
Local businesses can apply as an expansion so long as it introduces a new element in the current business.
Existing businesses must be Downtown Main Street members.
The contest boundaries are shown on the map

Official Rules & Regulations

Prizes are non-transferable and may not be redeemed for cash; substitutions by Prize Winner(s) are not allowed.
Printed copies of business proposals submitted into the contest may not be returned.
The Retail & Restaurant Challenge Judges will judge the business concepts and business plans. The Retail & Restaurant Challenge Judges will choose the winner(s)
By participating in this contest, you agree to these Official Rules and to all decisions of the Retail & Restaurant Challenge Judges, which are final and binding in all respects.
Red Wing Downtown Main Street reserves the right to use participant’s names, likeness, picture, portrait, voice, and written submissions and written or oral statements, for advertising and promotional purposes without additional compensation unless required by law.
By entering the contest, you validate the acceptance of a credit and background check in the first phase.
Winner(s) shall assume responsibility for the payment of all other items that are not part of the incentive package.
Winner(s) are required to have at least monthly contact with the Retail & Restaurant Challenge Judges prior to opening, in order to keep the Judges apprised of the progress.
In accordance with the IRS Code regarding prizes and awards, a Form 1099 may be issued by the Judges to the winner(s). Please consult your tax advisor for additional information.
Contingency rules for any loans/agreements shall be given, which is separate from the contest rules.
By accepting a Prize, the Winner(s) release and discharge Red Wing Downtown Main Street, the Retail & Restaurant Challenge Judges, their affiliated companies, participating sponsors, information providers, content providers, subsidiaries, advertisers, advertising agencies, promotional and marketing agencies, and any other companies involved with or otherwise providing services related to this promotion, and all their respective employees, officers, directors, representatives and agencies from the liability or damage due in whole or in part to the award, acceptance, possession, use or misuse of Prize or from participation in this Competition.
Information regarding the winner(s) will be posted on Red Wing Downtown Main Street’s website and will be released to the public.
The contest rules are not specifically bound by the category they are in (i.e., “Phase 1”). These category-separations are for easier reading of the rules.
The Retail & Restaurant Challenge Judges reserves the right to modify and/or extend the deadline dates.
Grant dollars can only be used on expenses that happen AFTER signing the contract with Downtown Main Street. No reimbursements will happen for expenses that happened prior to the contract start date.
If a Winner(s) is unreachable after 15 days, an alternate winner will be selected.
The judges reserve the right to take a phased approach and choose only one or two winners in the first round.
The Winner(s) will provide updated financial reports to Red Wing Downtown Main Street quarterly for the first two years of operation.

Winner(s)

The Winner(s) will be required to enter into a contract with Red Wing Downtown Main Street to receive awarded funds. Contracts will be issued following the conclusion of phase 2. The winner(s) will be reimbursed funds upon submission of receipts showing funds used towards agreed-upon eligible expenses. Funds may be applied in any manner that is consistent with business ideas presented in the sales pitch. The winner(s) must maintain a physical location from one year from their contract award date and within the Red Wing area from five years from their contract award date. This ensures that the business will open in the business district for at least one year and stay within Red Wing for five years. The winner will be required to do an interview with Downtown Main Street for promotional purposes of the event.