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Inventive tapas paired with flights from 100+ martinis fuel lively nights in sleek, moody digs at the heart of Madison’s State Street.
The Stuffed Olive - Madison stands out as State Street’s destination for inventive martinis and shareable small plates, blending a lively cocktail lounge atmosphere with chef-driven comfort food. Between its legendary martini list, late-night kitchen, and a knack for capturing Madison’s energetic spirit, this spot is a must for anyone wanting to experience the heart of the city’s modern nightlife and dining scene.
Recommendations based on quality, value, and visitor feedback
Item | Price |
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Fried Stuffed Olives
Signature house-stuffed olives, lightly breaded and fried, served with a zesty dipping sauce.
|
$10.00 |
Bruschetta
Toasted baguette topped with tomato, basil, and Door County cherry balsamic glaze.
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$9.50 |
Bacon Wrapped Jalapeños
Jalapeños stuffed with cream cheese, wrapped in bacon, and oven-roasted to perfection.
|
$12.00 |
Crab Rangoons (4)
Creamy crab filling in crispy wonton wrappers with a sweet chili dipping sauce.
|
$10.00 |
Spinach Artichoke Dip
Classic creamy dip served hot with pita points, featuring local Sassy Cow cream.
|
$11.50 |
Regular Charcuterie Board
Wisconsin cheeses, cured meats, house pickles, and artisan crackers for sharing.
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$18.00 |
Jumbo Charcuterie Board
An expanded version of the regular board, perfect for groups or celebrations.
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$30.00 |
Flatbreads (various)
Options include Crab Rangoon, Mediterranean Caprese, Pesto Chicken, Sweet & Spicy Sicilian, Spinach Artichoke, and Thai Chicken.
|
$13.50 |
Martini Flight (off-menu)
Three mini martinis of your choice, perfect for sampling the extensive cocktail list.
|
$15.00–$18.00 |
The Stuffed Olive concept began in 2006 in Cedar Falls, Iowa, where founders Chad and Angie Derifield set out to create a martini-focused lounge with a playful twist on classic cocktails and small plates.
Madison’s location opened in late summer 2022, bringing the brand’s signature martini culture to the heart of State Street. The Derifields chose this vibrant corridor for its foot traffic, college-town energy, and proximity to the Capitol and UW campus.
The building at 351 State Street has a colorful past, once home to The Double U sports bar and, decades prior, part of the State Street Arcade. The Stuffed Olive’s renovation uncovered early 1900s brickwork and transformed the space into a sleek, modern lounge with local art and a dramatic backlit bar.
Since opening, The Stuffed Olive - Madison has carved out a niche with its extensive martini menu, inventive small plates, and late-night kitchen—filling a gap in the local dining scene for upscale cocktails and shareable bites after hours.
Today, this location blends the Midwest hospitality of its Iowa roots with Madison’s creative spirit, drawing a diverse crowd of students, professionals, and visitors eager to experience a true State Street original.
State Street is fully pedestrianized, offering a lively, walkable environment day and night. Expect moderate crowds during weekdays and a surge of foot traffic on weekends, especially during university events and festivals.
The area is well-lit and patrolled, with a visible police presence on busy nights. Violent crime is near the national average—exercise normal caution and keep belongings secure, especially late at night during large events.
Tourism peaks in summer and during university breaks, with the biggest crowds flocking to State Street for the Art Fair on the Square (July), the Dane County Farmers’ Market (Saturdays), and Badger football weekends.
Downtown Madison is home to roughly 269,000 residents, a mix of students, young professionals, and long-term locals. The median age trends younger, and the area is known for its progressive, arts-focused community vibe.
Your guide to making the right choice
Cocktail lovers, small groups, date nights, and anyone seeking a lively, upscale-yet-approachable hangout on State Street. A top choice for pre-show bites, bar crawls, or late-night snacks with a creative twist.
You’re looking for a quiet meal during peak weekend hours, need guaranteed parking out front, or want a sports bar with TV screens. Large groups (6+) may face longer waits on busy nights.
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