This article is about the Proxi admin app at app.proxi.co. Its experience steps are for the experience editor released September 15, 2026; experiences built before then are legacy and have different screens.
Whatever your town calls it — a Sip and Stroll, Wine Walk, Wine Stroll, Beer Crawl, Brew Fest, Chili Crawl, Chili Fest, Chili Cook-Off, Cookie Crawl, Cocoa Crawl, Taco Trail, Taste of Downtown, Food Crawl, Girls' Night Out, Ladies' Night, Shop Hop, Holiday Open House, First Friday, or Art Walk — the shape is the same: people buy a ticket or grab a map, walk between downtown businesses, and get a pour, taste, or deal at each stop. It's one of the highest-return events a downtown can run, and it's a perfect fit for a map plus a passport.
The twist that makes this guide different from the festival one: the stops are businesses, and the businesses themselves know their offering best. So the winning setup is: get every business into your Listings, invite each one to their own portal, and let them keep both their business info and their event offering up to date — without you chasing anyone. Here's the whole build, using a made-up "Downtown Sip & Stroll" with 20 stops.
1. Get the Businesses Into Listings First
If you don't have listings for these businesses yet, this is the moment — listings are the shared profiles that make everything else (the map, the portal, next year's event) work without retyping.
On the Listings page, add each business with Add Listings — search for the business and we'll create the listing and pull in its details — or bring your whole participant roster in at once with Import a Spreadsheet or Extract From Text (paste the list) from the shortcuts in that dialog.
Select the new listings and click Get data to fill in hours, websites, and photos automatically.
Add a label like "Sip & Stroll 2026" so you can filter to this year's participants in one click. (See Setting Up Categories, Fields, and Labels.)
This is a one-time investment: next year's event starts with the roster already built.
2. Build the Event Collection and Map
Go to Maps → New Map, name it "Downtown Sip & Stroll," and under where the places come from choose Build one from your listings and check off the participants. The collection is made for you.
Add the event's own fields — click Fields → Add a field for each:
"What They're Pouring" (or "Chili Name," "Featured Cookie" — a text field for the offering).
"Event Deal" — the special-offer field for event-night discounts.
"Stop Number" — a Short code field, if you want numbered stops on the pins and the printed map.
Create a map from the collection. Set the Category options to match your event — Pour Stop, Bite Stop, Deal Stop, Check-In HQ — each with its own marker, and turn them on as filters.
Brand it in Branding (event name, colors, logo) and frame downtown as the starting view. Since this is a walking event, set Get directions to walking mode in Point Card → Actions.
3. Invite Each Business to Its Portal
Here's the part that saves you a hundred emails. Every listing can have a contact — the owner or manager — who signs into their own portal to manage their info:
Open each listing, add the owner as a contact, and click the invite button. You'll confirm — "Email them a link to sign in and manage this listing" — and they get a branded email with a Manage your listing button. They sign in with their email and a 6-digit code; no password to forget.
Once in, they can update their business information — name, description, hours, photos, and any listing properties — and those changes apply everywhere immediately.
They can also update their event info: on their portal page, your event collection shows with an Edit button that opens a form — "Edit your listing in Downtown Sip & Stroll" — pre-filled with their current entry, including "What They're Pouring" and their event deal. You choose whether those edits go live instantly or wait for your quick review (it follows the collection form's approval setting).
So the ask to each business becomes one sentence: "Click the link in your email, check your hours and photos, and fill in what you're pouring." You watch the map fill itself in.
4. Or Let Businesses Sign Themselves Up With a Form
Recruiting stops you don't have yet? On the collection's Public Form tab, switch on Let people add places and shape the form as your sign-up sheet: "Pour at the Downtown Sip & Stroll" with fields for their business, what they'll serve, and a contact email. Keep Check them before they appear on so you vet each stop, and share the form link in your business newsletter. Approved submissions land on the map; you can connect them to listings afterward. (See Collecting Places From Your Community.)
5. Ticket It and Gamify It
Go to Passports in the sidebar and pick the Bar Crawl template (or Food Trail for a cookie or taco crawl). Under Where should the places people visit come from? choose Use a collection you already have and pick your event collection, then Create & edit:
Sell tickets right at sign-up — under Registration → Pricing, click Set a Price for This Experience and choose One-time payment. Typical pricing runs $15 for food crawls up to $40+ for premium wine walks. Want a VIP tier and a cheaper designated-driver ticket? Build the event as a program with two ways to pay and use Add to an Existing Program instead. (See Charging to Join.)
Check-ins — under Check-in Rules, Code works beautifully here: each business gets a code on a card by the register ("POUR12" — set it on the place's row), and only wristbanded guests hear it. Or turn on QR code and use Print → Check-in QR codes for a sign per stop.
Chili cook-off or people's-choice voting? Two options. The quick one: on your map, turn on the Upvotes action in Point Card → Actions and rename it "Vote for this chili!" — every ticket holder's phone becomes a ballot, and you close voting by switching the action off. The proper one: build a Best Of from the Cook-Off Vote template on the same collection, with one ballot per person, Show Live Tallies for a race on the night, and a results export for the trophy. (See Best Of: Setting Up the Ballot and Voting.)
Badges — on the Badges tab, "Visited 10 Stops" (Earn when → Visit 10 stops) with a Completion message for a prize entry at check-in HQ, and the template's Full Crawl Club for finishing.
Click View as participant and walk a couple of stops before the night. (See Testing Your Experience Before You Launch.)
Built your experience before September 15, 2026? That one is a legacy experience with different screens, and its participation link starts with map.proxi.co. It keeps working without interruption, and there is nothing you need to migrate. The steps here are for the experience editor; the legacy tester steps are in Testing Your Challenge or Scavenger Hunt Before Launch.
6. Event Night
Run one central check-in table: ID check, wristband, tasting glass — and a big QR to the map. Stagger entry windows if you expect a crowd, so stop #1 doesn't get slammed at 5:00.
Small QR cards at each stop let people re-open the map (and check in) wherever they are.
Edits go live instantly — a business runs dry or closes early? Flip off Active on this map from your phone and the map stays truthful all night.
7. After the Event
Participants & Activity gives you check-ins per business (the foot-traffic proof that re-signs stops for next year — the recap ranks every place), Export → One row per person for your prize drawing, and who paid on the People view. Each business can also see its own numbers in its portal kit.
The voting tally crowns your chili champion — hand them a trophy they'll display all year.
And the durable win: every business now has a listing and portal access. Their hours and photos stay current year-round, and your next event starts from a live roster instead of a cold spreadsheet.
Beyond the Map: How Successful Strolls Run
Field notes from downtowns that run these every year:
Check local alcohol rules first — and early. Most cities require a special-event liquor permit (often 30–90 days of lead time), open-container laws usually only bend inside a defined boundary or social district, and expect requirements like non-glass cups, staffed boundaries, and carding anyone who looks under 30. Pair the permit with event insurance that covers alcohol — many cities require proof.
One wristband, one ID check. Central check-in means shop staff never have to card anyone — they pour for wristbands only. That single design choice is what makes 20 retail shops willing to host tastings.
15–25 businesses is the sweet spot. Main Street survey data puts the typical wine walk at ~20 stops, ~227 tickets at ~$28 average, with most districts charging businesses a small participation fee (~$75). Ask each stop for four things: staff the pour, offer an event-night deal, theme their space, and stay open the whole window. Shops that can't pour make great snack or activity stops.
Time it for weekend evenings in spring or fall — Friday or Saturday, roughly 4–9pm. Chili crawls own the cold months. Check the community calendar before you pick a date; a competing festival is the top attendance killer.
Market in waves: announce with early-bird pricing ~6 weeks out, reveal the business lineup ~4 weeks out (each reveal is a post), email the map 1–2 weeks out, and send day-of check-in details. Businesses cross-posting to their own followers is your cheapest reach — give them ready-made graphics.
Going the Girls' Night Out route? Flip the model: free or cheap admission, the draw is stacked shop deals and swag, with tastings as optional add-ons inside licensed venues — which also sidesteps most of the permitting.
Worth a read on the Proxi blog: the sip and stroll planning guide, the Downtown Kalamazoo Chili Challenge case study, how to host an ice cream crawl passport, and the Halloween pub crawl map guide. Beyond Proxi: Main Street survey data on downtown event economics, a model city handbook on special-event alcohol rules, and two live models to study: Downtown Bellingham's Wine Walk and Downtown Fond du Lac's Chili Crawl.