Back to School Gift Guide
For the teachers, coaches, and sitters who get your kids through the year — and for the household starting the routine over. One Downtown Madison Possibilities, over 50 local businesses to choose from. Delivered by email.


There are two lists this time of year — the crew who gets your kids through the year, and the household gearing up for a new one. A Downtown Madison Possibilities covers both.
Teachers, coaches, tutors, bus drivers, sitters, daycare staff — a local card they can spend on themselves.
over 50 local businesses — coffee, lunch, books, supplies, a treat. Their pick, not your guess.
Delivered by email. Dollars go straight to local Madison businesses.
These Madison businesses accept the Downtown Madison Possibilities Card — whether you're thanking a teacher or restocking your own school year.
A movie, a show, a night that isn’t about permission slips — Madison after the bell rings.
Nightlife
1 W. Dayton St., Madison, Wisconsin, 53703
Nightlife
636 State St., Madison, Wisconsin, 53703
Nightlife
116 W Mifflin St, Madison, Wisconsin, 53703
Nightlife
130 S Pinckney St., Madison, Wisconsin, 53703
Arts & Culture
100 N. Hamilton St., Madison, Wisconsin, 53703
Arts & Culture
201 State St., Madison, Wisconsin, 53703
For the week nobody has the energy to cook, and for the coach who stayed late. Madison’s kitchens, their pick.
Food & Dining
402 State St., Madison, Wisconsin, 53703
Food & Dining
111 S Hamilton St, Madison, Wisconsin, 53703
Food & Dining
122 W Mifflin St., Madison, Wisconsin, 53703

Food & Dining
468 State Street, Madison, Wisconsin, 53703
Food & Dining
116 King Street, Madison, Wisconsin, 53703
Food & Dining
418 State St, Madison, Wisconsin, 53703
Notebooks, a new reading list, shoes that fit this year — from local Madison shops instead of a big-box aisle.
Retail
230 State Street, Stop 1, Madison, Wisconsin, 53703
Retail
203 W Gorham St., Madison, Wisconsin, 53703
Retail
429 State St., Madison, Wisconsin, 53703
Retail
429 State St, Madison, Wisconsin, 53703
Retail
436 State St., Madison, Wisconsin, 53703
Retail
216 North Henry Street, Madison, Wisconsin, 53703
A haircut, a massage, an hour that belongs to them — the kind of thank-you a classroom mug has never been.
The first week of school books itself solid. Schedule delivery for the date and time you want — the morning of day one, the end of orientation week, or the Friday the new routine finally sticks.
Pick the delivery date during checkout. Done in under two minutes.

Pick an amount between $5 and $500.
Thank a teacher by name, or send a kid off with a word of encouragement.
Delivered by email or text — no shipping, no wrapping.
A Downtown Madison Possibilities lets the person you’re thanking choose what they actually want from over 50 local Madison businesses — coffee, lunch, books, a spa break. No more mugs or desk trinkets. It also supports local businesses and never expires.
Two lists, one card. The crew who gets kids through the year — teachers, coaches, tutors, bus drivers, sitters, daycare staff — and the household starting a new routine, including a busy-parent friend or a college kid heading back.
The Downtown Madison Possibilities is accepted at over 50 local businesses in Madison, including coffee shops, restaurants, bookstores, boutiques, salons, and more. They pick where and when.
Visit our purchase page, choose an amount ($5–$500), add a personal message, and send it by email — or print it for hand delivery on the first day. No shipping needed.
Yes. During checkout you can pick the date and time you want it delivered — the morning of the first day, the end of orientation week, whenever suits. Set it up early and skip the last-minute scramble.
No, the Downtown Madison Possibilities does not expire. They can use it whenever they’re ready — there’s no rush to spend it during the first week.
A Downtown Madison Possibilities for the teacher, the coach, or the parent holding it together — good at over 50 local Madison businesses. Delivered by email — no wrapping required.
Buy a Downtown Madison Possibilities