West Annapolis Business Association

10/14/2026

We’re so happy to feature Premier Planning Group, where thoughtful, personalized financial guidance helps make the complex simple and the future feel a little less complicated.

Whether you’re planning for retirement, preparing for a major life milestone, or thinking about the next generation, Premier Planning Group is dedicated to helping individuals and families navigate their financial goals with confidence.

Follow along as we continue sharing the people, places, and stories that make West Annapolis such a wonderful place.

📍 Annapolis, MD
🕒 Mon–Fri 9 to 5
🌐 premierplanninggroup.com

Read full story here: https://www.west-annapolis.com/featured-businesses/premierplanning

Great people make great businesses.



Premier Planning Group

10/07/2026

We’re so happy to feature Root to Bloom, a West Annapolis space where creativity, connection, and personal growth come together in meaningful ways.

We especially love the way Root to Bloom makes room for the complicated, beautiful work of growing—creating a place where girls, mothers, and women can explore who they are, connect with others, and find support along the way.

With a thoughtful blend of expressive arts, therapeutic insight, and community, Root to Bloom offers a welcoming space to grow from the ground up. We love their reminder that none of us has to figure it all out alone.

Direct link to their full story: https://www.west-annapolis.com/featured-businesses/roottobloom

📍 619 Ridgely Avenue, Annapolis · By appointment
🌐 roottobloomannapolis.com



Root To Bloom Annapolis

09/30/2026

No wind or rain could keep you away from this epic yearly party in the streets!

Such a great day! Wonderful people, impressive lederhosen, warm food, cold b**r, and cute pups.

Thank you to everyone who came out and made the West Annapolis Oktoberfest such a blast (no matter what!). See you next year, Annapolis!



Scarborough Capital Management
Travis Gray - Engel & Völkers
RAR Brewing
Chessie’s Wharf

09/29/2026

THANK YOU, WEST ANNAPOLIS!

The weather didn’t stop West Annapolis from showing up! We’re not deterred by a little Boat Show weather. Thank you to all of those amazing revelers who pulled on their foul-weather gear and came out to party!

And we really want to thank our crazy-good sponsors again! These are the people who help make it happen in a big way. Stop by and see them or just think of them fondly. We do! ❤️

Swipe through to see who we’re talking about. Can’t thank you all enough for another great Oktoberfest in beautiful West Annapolis, a town that looks good in the rain!

Great people. Great businesses. Doing great things.



RAR Brewing
Scarborough Capital Management
Chessie’s Wharf
Travis Gray - Engel & Völkers


Dockside Dermatology
Rob Tobin
Jack Martin Insurance Advisors
Lynbrook of Annapolis
Premier Planning Group
Rosso Commercial Real Estate Services

09/27/2026

09/27/2026

IT’S ON! WEST ANNAPOLIS OKTOBERFEST IS HAPPENING TODAY! 🍻
Come join us for one epic street party in beautiful West Annapolis!

📅 TODAY — Sunday, September 27
⏰ 11 AM–4 PM
📍 Annapolis Street & Giddings Avenue

We’ve got music, vendors, great food, superb seasonal suds, a VIP B**r Garden, happy people & premium porta-potties.

Dog-friendly. Family-friendly. Lederhosen-friendly.

Grab your friends, come party in the street, and celebrate Oktoberfest with us!

PROST! 🍻



RAR Brewing

09/27/2026

IT’S HERE! WEST ANNAPOLIS OKTOBERFEST IS TODAY! 🍻

Come join us for one epic street party in beautiful West Annapolis!

📅 TODAY — Sunday, September 27
⏰ 11 AM–4 PM
📍 Annapolis Street & Giddings Avenue

We’ve got music, vendors, great food, superb seasonal suds, a VIP B**r Garden, happy people & premium porta-potties.

Dog-friendly. Family-friendly. Lederhosen-friendly.

Grab your friends, come party in the street, and celebrate Oktoberfest with us!

PROST! 🍻


RAR Brewing
What's Up? Media
Visit Annapolis
Annapolis Maryland

09/26/2026

A HUGE Danke Shoen to Scarborough Capital Management!

We’re so grateful to have Scarborough Capital Management pitching in to help bring Oktoberfest to a street near you! Their team provides action-oriented advice for all your financial needs—helping clients make informed decisions and plan for their financial future.

They are longtime supporters of the West Annapolis Oktoberfest and one of the amazing hosts of this year's VIP B**r Garden! What would we do without you!

Great people. Great businesses. Doing great things.


Scarborough Capital Management

09/26/2026

KNOW BEFORE YOU GO! 🍻

Swipe through for everything you need to know for tomorrow’s epic Oktoberfest in beautiful West Annapolis!

📅 Sunday, September 27
⏰ 11 AM–4 PM
📍 Annapolis Road & Giddings Avenue

Vendors, food, music, happy people, superb seasonal suds & premium porta-potties.

Dog-friendly. Family-friendly. Lederhosen-friendly.

SEE YOU THERE!


RAR Brewing
Chessie’s Wharf
Travis Gray - Engel & Völkers
Scarborough Capital Management
Doppelgänger
The Capital
What's Up? Media
Visit Annapolis
Naptown Sings and Plays

09/26/2026

A HUGE Danke Shoen to our amazing 2026 Oktoberfest sponsors!

Swipe through to see the wonderful businesses and organizations who stepped up to help put on this epic street party!

We’re so grateful for your friendship and support. Great people. Great businesses. Doing great things.

HAPPENING TOMORROW!

📅 Sunday, September 27
⏰ 11 AM–4 PM
📍 Annapolis Road in beautiful West Annapolis

Vendors, food, music, happy people, superb seasonal suds & premium porta-potties.

Dog-friendly. Family-friendly. Lederhosen-friendly.

Come party in the street with us—and give a big DANKE to the people who help make it happen!



RAR Brewing
Chessie’s Wharf
Travis Gray - Engel & Völkers
Scarborough Capital Management
Dockside Dermatology
Rob Tobin
Jack Martin Insurance Advisors
Lynbrook of Annapolis
Premier Planning Group
Rosso Commercial Real Estate Services