Experiences
Curated experiences
in the heart of Old Town.
From guided wine tastings to intimate cultural evenings, each Cherry On Top experience is intentionally small, thoughtfully designed, and limited in seating.
Seats are limited. Advance booking is recommended.
View Upcoming ExperiencesWhat to Expect
We don't host events at scale —
we curate moments.
Our experiences are designed for guests who appreciate:
- Thoughtfully selected wines
- Intimate group settings
- Relaxed but elevated atmosphere
- Meaningful social connection
- Beautifully paced evenings
Whether you're joining us for a seasonal tasting or a special cultural night, every gathering is built to feel personal and memorable.
Upcoming Experiences
Explore what's coming next
Availability is intentionally limited to preserve the atmosphere of each gathering.
Uncork + Plant: Wine Bottle Terrarium Workshop
Uncork your creativity and design your own custom wine bottle terrarium.
Join us and Stop Shop & Prop for a hands-on wine bottle terrarium workshop! Create a custom planter using a prepped wine bottle and up to 5 premium, organically grown terrarium plants while enjoying your choice of wine or champagne.
- The Vessel: Custom-cut, prepped wine bottle planter
- Houseplants & Materials: Up to 5 premium, organically grown 2” terrarium plants
- The Know-How: Step-by-step design guidance from Stop Shop & Prop
- Includes first glass of wine or champagne (21+ only)
An evening of brush pen calligraphy
Slow down. Put the phone away. Let the ink do the talking.
An intimate workshop with @nataligraphy, you’ll leave knowing how to letter place cards, gift tags, and handwritten notes that people actually keep.
- hands-on guidance, no experience needed
- premium brush pens, yours to take home
- a workbook to return to, so the evening never really ends
- a glass of wine
Experience Types
Four ways to gather with us
🍷
Guided Wine Tastings
Educational but approachable tastings designed for both enthusiasts and curious beginners.
🌿
Seasonal Lawn Evenings
Weather-permitting outdoor gatherings that highlight the charm of our Old Town setting.
🎨
Cultural & Creative Nights
Select collaborations with artists and performers in an intimate format.
📖
Private Educational Tastings
Small-group wine education experiences available by request.
Important Notes
To maintain the quality of our experiences
- Seating is limited and often sells out
- Most experiences require advance ticket purchase
- Some events feature communal seating
- Outdoor events are weather dependent
- All wine events are 21+
We recommend booking early, especially for weekend dates.
Looking for Something Private?
Planning something more personal?
Cherry On Top offers fully curated private gatherings for small groups — tailored entirely around your occasion.
Explore Private EventsJoin the Guest List
Be the first to know.
Join our list for early access to new experiences, seasonal tastings, and limited-seat events.