Your Tallinn hit list: the top 5 events this week

18 May 2026 – 24 May 2026

Not sure where to be this week? Every week, in partnership with Gamma, we present a hand-picked selection of the five most compelling events taking place in and around Tallinn – it’s time to plan your week with purpose.

Introduction to portraiture in olis

The workshop, Pärnu 19, Tallinn

Tuesday 19 May, from 6pm

This is a small, focused workshop for anyone who wants to develop their craft the way the Old Masters did — working from a live model, taking the time to truly look and building an image with patience and intention. Sessions are typically three hours long, giving participants the space to move well beyond quick sketches and into something more considered and personal. Instruction is individual and adapted to each participant’s level, goals and preferred medium, whether drawing or painting, making it equally worthwhile for beginners finding their footing and experienced practitioners looking to deepen their technical vocabulary.

Your instructor, Kaspar Tamsalu, trained in rigorous easel painting at the Repin Academy of Fine Arts in St. Petersburg, previously led the Painting Department at Pallas University of Applied Sciences and works professionally as an Art Director and visual artist in the video game industry — bringing academic discipline and contemporary sensibility into the same room.

Easels and tape are provided at the venue. A full materials list for both painting and drawing is available in the event details.

International Dog Shows “Estonian Winner 2026”

Indoor arena, Eesti Jalgpalli Liit, Tallinn

From Saturday, 23 May to Sunday, 24 May

Estonian Winner 2026 & CACIB International Dog Show is one of the biggest canine events of the year, welcoming dog lovers from near and far for two days of breed showcasing, competition and everything in between. With over 2,000 dogs registered, it is a rare opportunity to meet breeds you may never have encountered before, chat with experienced long-term breeders and witness the kind of dedication that goes into showing a dog at international level. Doors open at 8:00 each morning, the official opening ceremony takes place at 9:45, and the rings get underway at 10:00.

Full details on the schedule, programme, and entry restrictions are available here.

EBS Padel x Pilates x Poké Bowl

Padel+, Rocca Haabersti 5, Tallinn

Saturday 23 May, from 2pm

Pilates x Padel x Poké Bowl is the last combo event of the year from EBS Spordiklubi and it is going out in style. The afternoon kicks off with a 50-minute pilates session — enjoyable movement, good energy and the perfect warm-up before things get competitive. From there, the group moves straight into a padel tournament with courts divided by level: Beginner, Beginner/Intermediate, and Intermediate/Advanced, so everyone gets a fair and fun game regardless of experience.

When the energy starts to dip, a fresh poké bowl will be waiting on site to restore it. This is not a serious tournament or a structured fitness class — it is an afternoon of movement, laughter and good company, wrapped up with food and the satisfaction of having done something genuinely enjoyable with your Friday. Bring your workout clothes and a good mood, and the rest is taken care of. Places are limited, and since this is the last one of the year, the excuse not to come is simply not there.

Writing in Tallinn meetup

Read & Kiosk 3, Põhjala tehas, Marati 5, Tallinn

Friday 22 May, from 10 am

Writing in Tallinn is back and this time it is happening somewhere with excellent coffee and the kind of atmosphere that makes you feel like you should be writing something important. The group meets for a two-hour session built around a simple idea: show up, write, talk a little, write some more and leave feeling like a person who has their life together. The format is friendly and the structure is light — a chat to ease in, two focused writing blocks with a break in between and a finish at noon that leaves the rest of the day entirely guilt-free. All styles welcome, which means your novel, your journal, your screenplay, your deeply personal essay that no one will ever read and whatever else you have been meaning to work on are all equally at home here.

Web3 Community Brunch

Basiilik Restoran, Lootsi 10-2, Tallinn

Friday, 22 May from 10 am

Whether you are deep in the Web3 space or simply curious about what all the fuss is about, this is a low-pressure opportunity to share a meal, have a real conversation and meet the people building things in Estonia’s blockchain and crypto community. Expect coffee, good food and the kind of informal exchange that tends to be far more useful than any structured networking event. All attendees also enjoy a permanent 10% discount on the menu at Basiilik using code EW3, courtesy of the venue partnership — so the brunch pays for itself a little.

And if you are still around in the afternoon, the same venue is hosting a Bitcoin Pizza Day celebration from 16:00, with free pizzas, drinks, and more networking opportunities. Reserve your place for the brunch here.

Tallinn Whisky show 2026

T1 Venue, Peterburi 2, Tallinn

Saturday 23 May, from 2 pm

Tallinn Whisky Show 2026 is back and if you have ever wanted to spend an entire day drinking exceptional whisky in the company of a thousand like-minded people, this is precisely the event you have been waiting for. With over 100 whiskies and premium spirits available for tasting, expert-led masterclasses and seminars, brand ambassadors on hand to talk you through their selections, a premium cigar corner, gourmet food and a charity lottery, the show manages to be educational, indulgent, and genuinely entertaining all at once.

Every ticket includes a tasting booklet to help you navigate the selection, entry to masterclasses and full access to the tasting floor — making it equally worthwhile for curious newcomers and seasoned connoisseurs who think they have already tried everything. They probably have not.

Full details on the schedule, masterclass registration, and tickets here.

Brought to you in collaboration with Gamma. Want more like this? Get Tallinn’s best events delivered straight to your inbox – three times a week, totally free. Just hit subscribe to join the Gamma newsletter.