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New Yorkers 1st Choice
Best of Walker's Point

Date spots for fun activities

Breaking the routine with someone special requires an engaging activity that keeps the conversation moving.

Based on 764 Opinions
+761
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Updated May 2026
01
Glassnote Candle Bar image 1
Glassnote Candle Bar image 2
Glassnote Candle Bar image 3
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Cozy space with a speakeasy vibe and chic decor invites intimate gatherings. Full-service bar offers remarkable cocktails alongside a unique candle-making experience. Guests engage with table games that encourage connection while candles cool.

Candle-making offers a fun and unique hands-on activity. Hosts are knowledgeable and engaging, making it a great option for date nights or groups.

Couples create custom candles together while sitting with a box of conversation questions that spark meaningful talks. This hands-on activity makes for a memorable date night or special occasion.

People are saying

"Making candles here is a really fun activity for everyone."

"It's a great place for a date night with a cool vibe."

"The cocktails here are delicious and super inventive."

Good to know

1

The candle-making experience costs $60 per person, plus drinks.

2

Reservations are recommended for groups to ensure availability.

3

The venue is located on the second floor with no elevator access.

02
Karaya Art LLC image 1
Painting studio

Painting studio offers step-by-step guidance with clear instructions and a warm, welcoming atmosphere. The space encourages a social and soulful experience with art-themed drinks and plenty of selfie moments. Classes suit all skill levels and foster a fun, interactive vibe for groups or individuals.

Painting sessions offer a fun and relaxing atmosphere with a warm, welcoming vibe. The host is energetic and supportive, making creative experiences enjoyable and rewarding.

Activities suit small date nights and parties. The setting offers a great date night experience with a relaxed vibe.

People are saying

"The instructor's clear, encouraging directions made this a fun activity."

"The art instructor's clear directions made painting enjoyable."

"It's a fun, welcoming atmosphere perfect for a date spot."

Good to know

1

The paint + sip events include all materials needed for participants.

2

Goodie bags are provided during special events like Easter.

3

Classes are designed to be fun and interactive for all skill levels.

03
Shaker's Cigar Bar & World Cafe image 1

Vintage bar with old-time speakeasy vibe and spooky decor offers indoor cigar smoking and a multi-level rooftop patio. Atmosphere feels haunted and immersive, enhanced by live jazz music and occasional ghost tours. Crowd enjoys a mix of cigar enthusiasts and those drawn to the unique ambiance.

Tours feature fun and energetic guides who make history engaging. Spirit interactions add a unique, enjoyable twist to the experience.

Dinner and drinks set the scene for a date night, paired with an infamous ghost tour that adds a unique twist. The carrot cake earns praise as a standout dessert, making the experience memorable.

People are saying

"The historical sites here are fascinating, especially the prohibition stories."

"The fun activities with Alexi were so energetic and spooky!"

"This ghost tour is a fun and interesting date spot."

Good to know

1

The ghost tour runs every weekend and requires advance reservations.

2

Expect a $10 entry fee for the ghost tour, payable at the venue.

3

The cigar bar allows guests to bring their own cigars without extra charge.

04
Caroline's image 1
Jazz club

Intimate jazz club with a cozy vibe and old school atmosphere. Live performances feature captivating jazz musicians delivering mellow, velvet-wrapped music. Space feels tight yet comfortable, creating a unique date night setting.

Cozy, chill vibes set the tone for fun live jazz music. Friendly staff add to the relaxed, enjoyable atmosphere.

Jazz music creates a unique atmosphere for date nights. The setting feels perfect for anniversaries and special occasions.

People are saying

"It's a cozy jazz bar with a really nice atmosphere."

"It's a great spot for a date if you love the live jazz music."

"The live music here is great and very entertaining."

Good to know

1

The band starts at 9:30pm on jazz nights.

2

There is a $12 cover charge at the door, payable in cash or card.

3

Parking is available in a free lot near the venue.

05
Anodyne Coffee Roasting Co. | Walkerโ€™s Point image 1

Industrial-chic space with cream city brick, wooden beams, and Edison bulbs creates a rustic, cozy atmosphere. Spacious yet inviting, it suits quiet work, casual conversation, and lively events with live entertainment. Communal tables and a stage foster connection and engagement among guests.

Events like Coffee Shop Astrophysics offer engaging and fun experiences. The bar staff create a lively and attentive atmosphere for guests during gatherings.

Offers a unique, affordable venue that welcomes LGBTQ+ couples. Hosts intimate events like weddings with a cozy, personal vibe.

People are saying

"I got married at this cafe; it was the perfect wedding venue."

"The venue coordinator Erica made planning our wedding day stress-free."

"Erica and her team made our wedding vision a magical reality."

Good to know

1

Parking can be challenging; consider arriving early or using nearby street parking.

2

Live music events occur on select Saturdays, check the schedule for details.

3

Expect a lively atmosphere during popular events, with limited seating available.

06
Indulgence Chocolatiers image 1

Chocolate shop offers handcrafted delicacies with creative flavors and woodwork interior. Atmosphere suits intimate gatherings and classes with detailed, educational pairings. Selection includes limited vegan options and focuses on unique chocolate experiences.

Classes offer themed pairings with wines, liquors, and cocktails in just the right size groups. Events focus on paired chocolates and bourbons, creating a fun and engaging atmosphere.

Perfect for a date night with a Walkerโ€™s Point vibe. The chocolates include some that stand out as lifetime best. Spending a couple hundred dollars is common here.

People are saying

"I loved the wine and chocolate pairings; they were a super fun evening."

"These fun activities, like cocktail and chocolate pairings, were a blast."

"These Date Spots have chocolates that are the coolest ever."

Good to know

1

They offer themed pairing classes with wines, liquors, and cocktails.

2

Educational tastings describe the chocolates and pairings in detail.

3

Flights pairing wine or beer with chocolates are available.

07
The Iron Horse Hotel image 1

Former factory building offers vintage motorcycle-themed design with stylish loft-style rooms and an inviting beer garden. Atmosphere blends modern elegance with historic charm, creating a relaxed and social vibe. Quiet, comfortable rooms complement lively bar and pool table area for casual gatherings.

Fun comes from the pass through door connecting the bar to the outdoor deck, creating a lively flow. The overall vibe feels sexy and energizing, making it a great spot for a mini staycation.

Offers a cozy setting for couples celebrating special occasions like birthdays or anniversaries. Frequent visits highlight its appeal as a quiet getaway and a spot tied to meaningful memories such as weddings.

People are saying

"The beds were really comfortable and the rooms were nice and spacious."

"It's a special place for a romantic night away."

"The live music and biker-themed lobby make for a fun atmosphere."

Good to know

1

Parking in the parking ramp costs over $30 per day.

2

There is no free parking available at the hotel.

3

The hotel hosts a bike night every Thursday evening.

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Walker's Point, Milwaukee

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