# Events & Things To Do In Oakland, MD This Weekend | May 22-24, 2026| AllEvents

- **Subtitle**: Oakland, Maryland is a city full of experiences, activities and events. Explore some of the best things to do in Oakland, Maryland this weekend and make your Friday, Saturday and Sunday full of fun and excitement.
- **Category**: Weekend
- **Display Name**: Events this weekend
- **Type**: time_filter

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## About

Weekends become special if you know how to make the most out of it. There are a lot of fun things to do and events in [CITY] this weekend for you to explore.

Make your weekends memorable. Check out all upcoming weekend events in [CITY].

## Weekend Events in Oakland

- **Event Name**: Memorial Day Weekend Craft and Vendor Show
  - **Description**: Stop by for our weekend Memorial Day Craft and Vendor Show!
10-3pm each day with many talented vendors! 
🍞Bakers
🎨Painters
🧶Crocheters
🪢Home Decor
And so much more!
  - **Interested Audience**:
    - Count: 104
  - **Date**: Sat May 23 2026 at 10:00 am – Sun May 24 2026 at 03:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/memorial-day-weekend-craft-and-vendor-show/200029985734244
  - **Venue**: 18268 Garrett Highway, Oakland, MD
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy9kNTUxOTMzM2NlNDE2Yzk3MmY0ZjNmYzgyNDA1ZGJlZTJjNTdmZTUyMDc0OWJmZDBjYmFiZjQ3NGRhNGU3M2RjLXJpbWctdzEyMDAtaDY3Ni1kY2JmYmVjMC1nbWlyP3Y9MTc3NzczMjM3Nw.avif
  - **Categories**: memorial-day
- **Event Name**: Thomas' Retro Game Challenge!
  - **Description**: Director Thomas Vose presents Thomas' Retro Game Challenge! at the Main Library on Saturday, March 23rd at 1 PM. Participants will compete in games from the 80s and 90s - maybe even earlier! Which games? You'll have to join us to find out! 

Bonus! A gent
  - **Interested Audience**:
    - Count: 6
  - **Date**: Sat May 23 2026 at 01:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/thomas-retro-game-challenge/200030040982117
  - **Venue**: 6 N Second St., Oakland, MD, United States, Maryland 21550
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9kMGRjMDFhNDhkNGNmYzlmYmNlYzA1NzNmYjE5MTU2NmY5ZTljYTJkZjIwN2YwYzI4OTRkZjE1MDA2ZDg0YTE2LXJpbWctdzEyMDAtaDYyOC1kYzAzMTYzMi1nbWlyP3Y9MTc3ODM4NjI3Ng.avif
  - **Categories**: contests
- **Event Name**: Live music with Scott Ross
  - **Description**: Come and enjoy one of our favorite local singers here at the lounge, Mr. Scott Ross. If the weather is nice, music will be outside by the fireplace.
  - **Date**: Fri May 22 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/live-music-with-scott-ross/200030085482554
  - **Venue**: 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9kZjk1NjI2Nzg1MmI1ZDYzZTM4ZTQ5ZGNkMThmYzRhMzUyNGVmNGQ2OTQ1MGMxN2FkNmM5ZDljOWFmMjhhNjUwLXJpbWctdzYzOC1oOTYwLWRjZDlkOWQ5LWdtaXI_dj0xNzc5MzM2Mjkz.avif
  - **Categories**: Music, Entertainment
- **Event Name**: Yoga & Sip
  - **Description**: Have you ever done yoga at a bar? Come and enjoy a free half hour of gentle yoga right in the lounge! All are welcome. This month donations will be accepted for local charity Int's In The Bag.
  - **Date**: Sat May 23 2026 at 11:30 am (-04:00)
  - **Event URL**: https://allevents.in/oakland/yoga-and-sip/200030085482052
  - **Venue**: 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9iYWEyN2M4Njk4MjA2NzRlMDdkM2VkYTJjYWU4OTMyMjM4MzdjMGE5ZWExZTNlODMzOWUyMjllOTNmZTU5YTkxLXJpbWctdzEwMDAtaDY2Ny1kY2Q3ZGFkYS1nbWlyP3Y9MTc3OTMzNjI5Mg.avif
  - **Categories**: health-wellness, Nonprofit
- **Event Name**: Live Music with Dan Bourdeaux
  - **Description**: We are lucky to have Dan Bourdeaux back again in the lounge for an evening of live music. You won't want to miss it! If the weather is nice, music will be outside by the fireplace.
  - **Date**: Sat May 23 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/live-music-with-dan-bourdeaux/200030085479845
  - **Venue**: 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8yNjQxZTI1MGQ3MzNkMzgwZDQxMTRiOTcwYzg5YTBkYzk0NDI4YzlhOTZhODVkMWU2YTA4YjU4NTY1YWI2MTJmLXJpbWctdzEyMDAtaDEyMDAtZGMxNzE1MTUtZ21pcj92PTE3NzkzMzYyODU.avif
  - **Categories**: Music, Entertainment
- **Event Name**: Family Sundays! $5 Admissions
  - **Description**: Join us on Sundays for family fun! $5/person admission. Under 1 year of age is still free!
  - **Date**: Sun May 24 2026 at 01:00 pm – Sun May 24 2026 at 05:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/family-sundays-$5-admissions/200030085480146
  - **Venue**: 115 South 2nd St., Oakland, MD
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9kNWY0YjJjNWMzYmNmMTY0MDY4ZGU2NDVhYjE1OTUxY2JjYjU3NjAwOGU1NDBmOGM1MWIzNGQ1ZGE2MGNjMzQ0LXJpbWctdzEyMDAtaDE2MDAtZGM5Nzg5NzAtZ21pcj92PTE3NzkzMzYyODU.avif
- **Event Name**: Open Mic Night
  - **Description**: Come in a share your talents with other local musicians. If the weather is nice, music will be outside by the fireplace.
  - **Date**: Sun May 24 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/open-mic-night/200030085480548
  - **Venue**: 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy8yYTVmMzAyOTdhNWMwZTI1ODk4Yzg0YmQ0OTQ1MDYxNzVjOGNiZTQ5Y2ZkMjk0NzI2NDZmNjA5NTA3MGFmYTg1LXJpbWctdzgyMC1oMzEyLWRjYzJhNjFmLWdtaXI_dj0xNzc5MzM2Mjg3.avif
  - **Categories**: Music, Entertainment
- **Event Name**: CUSTOMER AND COMMUNITY APPRECIATION DAY
  - **Description**: 🎊🎉🎊🎉 COME JOIN US  🎊🎉🎊🎉
  - **Date**: Sat May 23 2026 at 11:00 am – Sat May 23 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/customer-and-community-appreciation-day/200030051277341
  - **Venue**: Broadford Park
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy84Y2NjNmJhNzUzZDIxMjM3N2IwOGFlYjRlMDBkMGY5MWI4M2JhMmE5ZjkzZDBiMzRlYWNhNGI5ZDQwZTAyMzMwLXJpbWctdzEwODAtaDEzNTAtZGMwMzE1NGYtZ21pcj92PTE3Nzg3MjgxMjE.avif
- **Event Name**: Living Well with Chronic Conditions & Pain Self-Management Programs
  - **Description**: Join GRMC’s Care Management Team for our NEW Living Well with Chronic Conditions and Pain – Self-Management Programs 💙

These FREE 6-week classes provide proven tools and support to help you better manage chronic conditions, reduce pain, and improve your
  - **Date**: Fri May 22 2026 at 10:00 am – Fri May 22 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/oakland/living-well-with-chronic-conditions-and-pain-self-management-programs/200030085480848
  - **Venue**: 251 N Fourth Street, Oakland, MD, United States, Maryland 21550
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy8zZjUwZjYzZWYzOTljNjI2ODUyMWE1YWNhYjcwZmU5NmNhZjc1YWQzNTBmNTViYjY5ZTgyNmIzMThkYjQ2MjM4LXJpbWctdzk0MC1oNzg4LWRjZjNmM2YxLWdtaXI_dj0xNzc5MzM2Mjg4.avif
  - **Categories**: Workshops, health-wellness

## Trending Events in Oakland

- **Event Name**: All About The Bay Quarterly Workshop
  - **Description**: Master Your Pitch Workshop for Entrepreneurs Theme:Today is about creating a breakthrough in how you communicate your purpose, business, and value — from stakeholder meetings, to your website messaging, to confidently recordi
  - **Venue**: OAK - Informal Spaces (formerly Port Labs)
  - **Banner**: https://cdn2.allevents.in/thumbs/thumb6a07671781764.jpg
- **Event Name**: Ariana Grande at Oakland Arena
  - **Description**: ✨ Embark on an extraordinary journey at Ariana Grande at Oakland Arena, where every moment promises to be unforgettable! 🌟 Imagine of transforming Oakland Arena in the heart of Oakland, CA
  - **Venue**: Oakland Arena
  - **Banner**: https://cdn-az.allevents.in/events1/banners/1cec7af0-870d-11f0-90cd-497b426e00a4-rimg-w1200-h800-dc8e9090-gmir.jpg?v=1756715084
- **Event Name**: J Cole at Oakland Arena
  - **Description**: 🎉 Prepare to be amazed at J Cole at Oakland Arena, the most anticipated gathering of the season! 🌟 Set against the stunning backdrop of Oakland Arena in vibrant Oakland, CA, this event p
  - **Venue**: Oakland Arena
  - **Banner**: https://cdn-az.allevents.in/events9/banners/ad4144d0-3259-11f1-9977-69abb8414888-rimg-w776-h1200-dc010101-gmir.jpg?v=1775549616
- **Event Name**: Ariana Grande
  - **Description**: 📍 Venue: Oakland Arena
🏠 Address: 7000 Coliseum Way, Oakland, CA 94621
🌆 City: Oakland
📍 Location: 37.7503, -122.203✨ Experience the magic of Ariana Grande, where moments become memories that last a lifetime! 🏛️ The iconic Oaklan
  - **Venue**: Oakland Arena
  - **Banner**: https://cdn-az.allevents.in/events5/banners/80a5eda0-51e3-11f1-be3c-5d1f450c2704-rimg-w1200-h900-dc2f2f45-gmir.jpg?v=1779017298
- **Event Name**: J. Cole
  - **Description**: 📍 Venue: Oakland Arena
🏠 Address: 7000 Coliseum Way, Oakland, CA 94621
🌆 City: Oakland
📍 Location: 37.7503, -122.203🌟 Step into a world of wonder at J. Cole, where extraordinary moments await! 🏛️ Located at Oakland Arena
  - **Venue**: Oakland Arena
  - **Banner**: https://cdn-az.allevents.in/events10/banners/157b7b30-1471-11f1-8750-ff9743e5691c-rimg-w1200-h800-dc01a27e-gmir.jpg?v=1772261135
- **Event Name**: Olivia Rodrigo at Oakland Arena
  - **Description**: 🎉 Welcome to Olivia Rodrigo at Oakland Arena, where dreams come alive and possibilities are endless! 🏛️ Join us at Oakland Arena in the heart of Oakland, CA for an event that defies expe
  - **Venue**: Oakland Arena
  - **Banner**: https://cdn-az.allevents.in/events4/banners/931cb980-4e66-11f1-9403-c734ca7258ad-rimg-w1200-h675-dc1f1a20-gmir.webp?v=1778633788
- **Event Name**: Olivia Rodrigo - Oakland, CA
  - **Description**: Olivia Rodrigo announces 'The Unraveled Tour' w/ Wolf Alice, The Last Dinner Party, Grace Ives, #DieSpitz & #DevonAgain → https://tinyurl.com/orodrigotickets
  - **Venue**: Oakland Arena and Oakland-Alameda County Coliseum
  - **Banner**: https://cdn-az.allevents.in/events3/banners/40057dc97ffa577e135fad52958a93c97967094916ae4b66e9dd5b456f8ada84-rimg-w942-h628-dcb9a8e0-gmir?v=1779036996
- **Event Name**: Jill Scott
  - **Description**: 🌟 Journey into wonder at Jill Scott, where extraordinary experiences await around every corner! 🏛️ Set against the backdrop of Paramount Theatre - Oakland in dynamic Oakland, CA, this eve
  - **Venue**: Paramount Theatre - Oakland
  - **Banner**: https://cdn-az.allevents.in/events2/banners/0f95f200-23d4-11f1-8500-4f0c3b0bf48e-rimg-w1200-h675-dc434b17-gmir.jpg?v=1773952912
- **Event Name**: ENHYPEN at Oakland Arena
  - **Description**: 🎉 Prepare to be amazed at ENHYPEN at Oakland Arena, the most anticipated gathering of the season! 🌟 Set against the stunning backdrop of Oakland Arena in vibrant Oakland, CA, this event
  - **Venue**: Oakland Arena
  - **Banner**: https://cdn-az.allevents.in/events4/banners/33e73fc0-3d05-11f1-aafe-8d25a272ea36-rimg-w1200-h581-dc131306-gmir.jpg?v=1776722798

## Browse Weekend Events by Date

- [Weekend Events Today in Oakland](https://allevents.in/oakland/this-weekend--today)
- [Weekend Events This Weekend in Oakland](https://allevents.in/oakland/this-weekend--this-weekend)
- [Weekend Events in May in Oakland](https://allevents.in/oakland/this-weekend--may)
- [Weekend Events in June in Oakland](https://allevents.in/oakland/this-weekend--june)

## FAQs

- **Q**: What are the top Weekend events in Oakland?
  - **A:** Memorial Day Weekend Craft and Vendor Show (Sat May 23 2026 at 10:00 am at 18268 Garrett Highway, Oakland, MD), Thomas' Retro Game Challenge! (Sat May 23 2026 at 01:00 pm at 6 N Second St., Oakland, MD, United States, Maryland 21550), Live music with Scott Ross (Fri May 22 2026 at 06:00 pm at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550), Yoga & Sip (Sat May 23 2026 at 11:30 am at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550), Live Music with Dan Bourdeaux (Sat May 23 2026 at 06:00 pm at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550).
- **Q**: What Weekend events are happening in Oakland this weekend May 22–24, 2026?
  - **A:** Memorial Day Weekend Craft and Vendor Show (Sat May 23 2026 at 10:00 am at 18268 Garrett Highway, Oakland, MD), Thomas' Retro Game Challenge! (Sat May 23 2026 at 01:00 pm at 6 N Second St., Oakland, MD, United States, Maryland 21550), Live music with Scott Ross (Fri May 22 2026 at 06:00 pm at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550), Yoga & Sip (Sat May 23 2026 at 11:30 am at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550), Live Music with Dan Bourdeaux (Sat May 23 2026 at 06:00 pm at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550).
- **Q**: What Weekend events are happening in Oakland in May 2026?
  - **A:** Memorial Day Weekend Craft and Vendor Show (Sat May 23 2026 at 10:00 am at 18268 Garrett Highway, Oakland, MD), Thomas' Retro Game Challenge! (Sat May 23 2026 at 01:00 pm at 6 N Second St., Oakland, MD, United States, Maryland 21550), Live music with Scott Ross (Fri May 22 2026 at 06:00 pm at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550), Yoga & Sip (Sat May 23 2026 at 11:30 am at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550), Live Music with Dan Bourdeaux (Sat May 23 2026 at 06:00 pm at 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550).
- **Q**: How can I find Weekend events in Oakland?
  - **A:** You can discover upcoming Weekend events in Oakland on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for Weekend events in Oakland?
  - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets.
- **Q**: What are the popular venues for Weekend events in Oakland?
  - **A:** Some popular venues hosting Weekend events in Oakland include 18268 Garrett Highway, Oakland, MD, 6 N Second St., Oakland, MD, United States, Maryland 21550, 119 S. 2nd Street, Oakland, MD, United States, Maryland 21550.
- **Q**: Who are the top organizers for Weekend events in Oakland?
  - **A:** Popular organizers hosting Weekend events in Oakland include Brodak's Banquet Hall, Ruth Enlow Library of Garrett County, The Green Room Lounge.
- **Q**: Are there any online Weekend events available?
  - **A:** Yes, many Weekend events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere.
- **Q**: How can I get notified about new Weekend events in Oakland?
  - **A:** Follow the Weekend category on AllEvents.in to get notified when new Weekend events are listed in Oakland.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/01/bac113436441a783feaca7074943a8/this-weekend.webp

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