A guitar retreat in Portland - 19th to 25th September

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Let’s pack for Portland, shall we? 

We can’t wait to get to Portland. It’s been on the list for a long time, and for a number of reasons. There’s a rich music history there, as we will discover in our daily workshops, and in recent years has become a mecca of independent music, venues and creativity. It has a reputation as being slightly hipster, which I think comes from its rich heritage of crafts and DIY ethos. As a result, in putting together this itinerary, we were really spoilt for choice and I imagine when we get there, the daily plans will evolve, as they always do in the most exciting cities as people drop in suggestions over breakfast every morning. 

A real highlight of the 2025 retreats season, this one. Hope to see you there. 

What you get

• Course materials, song sheets and historical information in PDF format to accompany all workshops and your time in the city

• A Guitar Social guide to the dive bars and where the locals eat

• A concierge service from The Guitar Social as well as a daily itinerary

• Fourteen hours of workshops specific to Nashville and the music it has generated 

• A space in the best accommodation we can find

• Breakfast daily 

• Entrance to The Shanghai Tunnels 

• Tickets for the walking tour of Portland 

• Entrance and tickets for the brewery tour

How many people will be there

We limit it to about 15. This is a far cry from a guitar retreat in a conference room in a hotel on the motorway. This is small scale, boutique, bespoke.

What we’ll do 

The daily plan detailed below change based on the local knowledge we pick up on the ground and your suggestions. Sometimes, the day takes on its own mood, and we follow the breeze wherever it sends us.

What’s the theme of the day?

The itineraries and workshops are carefully selected to give each day its own mood and tone. Workshops are built to match where we might be going. A good example in this itinerary is day four, psychedelic workshop followed by an ice cream lunch and a trip to a witches castle. 

Some days will be silly, wild and fun, some days will be about learning, some days will be restful. By the end of the trip, you will feel like you’ve been on a real journey that is centered around music, connecting and exploration. 

Day 1 : 19th of September 

Theme of the day-travel and rest

4:00 PM – Arrival in Portland. We’ll meet at the accommodation, take some time to settle in and toast our trip with some drinks courtesy of The Guitar Social.

5.00pm-  A walk around the neighbourhood, Pizza, decompression. It was a long flight, but you’re looking great and we have an incredible week ahead of us.

7.00pm Workshop #1-What the hell are we doing in Portland?! A two hour journey through the key artists to have worked, created and emerged from Portland. 

Day 2: 20th of September 

Theme of the day-Independence and less travelled routes

8.30 AM – Breakfast at the accommodation

9.00 AM Workshop #2  Indie Foundations: Playing the Portland Sound

12:00-2:00 PM Walking music history tour of Portland 

4:00 -5.30PM Shanghai Tunnels with beer tasting. Underneath China town there is over 14, 000 square foot of interconnecting tunnels. This tour takes you through them. Full of anecdotes, ghost stories and with a free pint at the end. 

7:00PM Dinner at White Eagle Saloon, accompanied by live music

Day 3: 22nd of September 

Theme of the day-Grunge/Hipster/DIY

8:30 AM – Breakfast at the accommodation

9:30 AM –Workshop #3  Morning Guitar Workshop- Portlands  Grunge Roots. Power Chords, heavy riffs and the influence of Portland's grunge music across America and the world. 

12:30 PM – Lunch Food carts at Pioneer Courthouse Square.

2:00 - 5:00PM   Downtown with Powells Book Store on the must see list, the Worlds largest book store which is so big, it covers an entire block. If you’re not a book worm, don’t worry, we are in downtown, a hipsters mecca. Go get a capacho choo and have your beard oiled and we’ll catch you later.

You’ll find lots of shops and places to hang out. The group will stay together, and then perhaps drift apart as we each go in search of the place in downtown we like the look of from our personal research. 

This is a vital few hours, as we become more familiar with the City and start to feel like we know how it works. 

Free time-The City is yours, go and explore.  You may wish to consult the Guitar Socials off the beaten track guide detailing dive bars, local places to eat and shops on the must see list which are not included in our group plans. 

7:00 PM -Misdeminour Meadows A mini Guitar Social take-over at this bar where you, yes YOU, get the chance to play live. 

Day 4: September 21

Theme of the day- Psychedelic adventure*

8:30 AM – Breakfast at the accommodation

9:30 AM – Workshop #4-Psychedelic Jam Workshop. Admittedly, it’s a little early in the morning to start tripping out with some cosmic jams but that’s exactly what we are going to do, celebrating the great jam bands of Portland by doing what they do, but better. Of course. 

1:00 PM – Lunch Lunch today is Ice Cream at the Salt and Straw. Vegan options available. And yes, we are having Ice Cream for lunch.

2pm-4pm The Witches Castle in Macklay Park. Mackplay park is an inner city oasis featuring a building described as one of the creepiest abandoned buildings in America, The Witches Castle. 

5:00pm Drinks at The Happy Landing. A gem of a dive bar. The Guitar Social loves, LOVES, a dive bar, and we can’t wait to check this one out. 

8:00 PM – Live Blues Show at The Blue Diamond, an off the beaten track bar that rates very highly 

Day 5:23rd of  September

Theme of the day-Roots and history

8:30 AM – Breakfast at the accommodation

9:30 AM – Workshop #2 Pacific North West Blues. Featuring slide guitar basics, gritty licks and slow burn solos.  Please bring a slide to take part in this workshop. 

1:00PM- Lunch close to our next stop-quick, easy, think street food

 2:00 PM  Oregon Historical Society for exhibits on Portland's history allowing us a deeper understanding of the city.  Exhibits vary, but music exhibits feature heavily on the rota so with some luck, we should find something with a musical element. 

Free time-The City is yours, go and explore.  You may wish to consult the Guitar Socials off the beaten track guide detailing dive bars and local places to eat. 

6pm  Dinner and live music from McMenamins Kennedy School. Here’s a bit from their website 

Note from the owner of McMenamins ‘Remember when the worst thing you could imagine was being kept after class? My, how things have changed! At Kennedy School, you'll never want to leave. You can have a pint in a classroom, enjoy an aged whiskey in detention, enjoy a movie in the old auditorium.... The possibilities here are endless. (Just don't run in the hallways, please. You might spill your beer’ 

This historic and wonderful venue has nightly live music shows, so we’ll be hanging around to see what’s happening. 

Day 6: 24th of September 

Theme of the day: YOU! 

9:00 AM  Workshop #’7 Alt Country, thriving in Portland enjoyed with breakfast

Free time-The City is yours, go and explore.  You may wish to consult the Guitar Socials off the beaten track guide detailing dive bars, local places to eat and shops on the must see list which are not included in our group plans. 

2.00 PM  Lunch & Brewery VisitLunch at Deschutes Brewery with a tour and tasting

Free time-The City is yours, go and explore.  You may wish to consult the Guitar Socials off the beaten track guide detailing dive bars, local places to eat and shops on the must see list which are not included in our group plans. 

7:00 PM – Jam Session  at Artichoke Music where food is also served. 

Note from Thomas ‘’Artichoke is basically The Guitar Social, but in Portland. They have a great community of people learning, hanging out and doing events. There was me thinking we are along in our endeavours! They are also expect us, so I’m looking forward to this one’’

Day 6: September 25th

Theme of the day-looking back, looking forward

8:00 AM – Breakfast at  the accommodation

8:30 AM – Workshop - Final session: Workshop #7 Review of the week

12.00 PM Bag drop off at a local hotel or bag drop off point

12:30 PM – Lunch and Reflection Le Pigeon. A good place to celebrate an awesome week where the reunion will be organised at a bar in London a few months down the line. 

Goodbyes, see you soons, and to the airport. 

 Accommodation:  

How the accommodation works

We only ever take the finest accommodation we can find. This involves big spaces in high end houses and apartments. Rooms are generally shared and room shares are allocated empathetically based on age, interests and gender. It is worth mentioning, the time spent in your room is likely to be very little. 

Limited solo rooms are available, with the price listed below. 

Prices 

• Double in a room that contains one other double  £1292

• Double in a room that contains two singles £1222

• Single in a room that contains one other single and one double £1192

• Single  in a room containing one bunk bed-this option is not the bunk bed  £1085

• Your own room £1967

Confirming the trip, refunds and flights

Our retreats always sell out, however, we don’t confirm the trip until we have reached 70% of the bookings. At this stage we provide a suggested flight. We aim to do this 3 months before departure. It is often before 3 months that we hit this mark.  

Trends in flight prices are showing that flights booked 3 or so months before departure can be cheaper than 12 months ahead. 

If the trip hasn’t reached 70% at the 3 month mark, we will be in touch to have a conversation. 

It is worth noting that in our ten year history 100% of our retreats have gone ahead. 

In the highly unlikely event that a trip doesn’t go ahead, you will be issued a refund. 

You can cancel your trip and receive a refund at any point up until the 3 month period before departure date arrives.  After that, refunds are not offered, but, credit with The Guitar Social Retreats on an alternative trip can be explored. 

We kindly ask that you do not make any efforts to sell your ticket within The Guitar Social community and instead, talk with us directly. 

Getting to the accommodation

When the trip is confirmed, you’ll be provided with an address. Your job is to get to that address, once there, your trip with The Guitar Social begins. 

You may also join a whatsapp group where you can organise to share an airport transfer. 

Booking today

You can book in full up to six months before departure for a 5% discount on the price. 

Otherwise, we require 20% with the remaining balance paid 6 months before departure. 

To book, email thomas@theguitarsocial.com