Free stock footage via Coverr

Three estates. One standard of belonging.

Boutique lodging, curated events, executive retreats and strategic consulting across Bethesda, Cabin John and downtown Annapolis.

The Oaks InnAnnapolis

Events & venue

Rooms that hold the occasion.

Weddings, receptions, board sessions, design charrettes, film shoots and family milestones. Every booking is planned end to end — catering, layout, staffing and flow — so the day runs without a seam.

  • 01

    Corporate off-sites

    Strategy sessions, partnering workshops and leadership retreats in a setting that encourages people to actually talk to one another.

  • 02

    Private celebrations

    Milestone birthdays, showers, receptions and reunions, with in-house catering from a chef with forty years in the family business.

  • 03

    Photo & video production

    Multiple interiors, gardens, terraces and canal-side exteriors — Cabin John was built for the camera.

  • 04

    Wine, cigar & tasting evenings

    Outdoor cigar lounges, heat lamps and fire pits, paired by a wine enthusiast who takes pairing seriously.

150Indoor & outdoor guests
75Seated indoors
16Overnight guests
3Estate venues

Retreats & wellbeing

Where teams think and people restore.

The same houses that host a strategy session on Thursday host a couple reconnecting on Saturday. Wellness is built into the property, not added to the invoice as an afterthought.

Spa & body

In-house therapies

Massage and bodywork delivered on property, so no one leaves the estate to reset between sessions.

Plan a retreat

Energy & practice

Reiki, crystal healing, yoga

Yoga deck and guided practice for individual self-care days, team wellbeing programs and couples retreats.

Plan a retreat

Leadership

Executive strategy sessions

Facilitated planning and training in a tranquil setting that makes reflection and honest dialogue possible.

See consulting

SJB Diversity Management

Strategy, compliance and community engagement.

Formerly Indigo Mid-Atlantic. We assess the work an organization is already doing, build a strategy that fits its mission, and leave behind a plan people can actually execute — with the compliance record to match.

Led by a Georgetown Law graduate with senior policy and leadership experience across national companies, universities and local government.

  • 01

    Strategy & assessment

    Organizational assessment, tailored strategy, and actionable plans aligned to mission and goals.

  • 02

    Interactive workshops

    Belonging, unconscious bias, cultural competency and inclusive leadership — delivered on-site at the Inns.

  • 03

    Compliance

    Federal, state and contractual requirements, including subcontractor management and reporting.

  • 04

    Community engagement

    Partnering sessions, design charrettes, public engagement and public-private partnership planning.

  • 05

    Project management

    Project, construction and energy management through the group's dedicated PM division.

Spoken word & keynotes

The Weight & The Wonder

A 10–15 minute spoken word performance by Sharon Jackson Wilder, Esq. on raising Black sons, entrepreneurship, partnership and legacy. Delivered over live or recorded jazz accompaniment, with an optional audience conversation or keynote discussion.

I

The Weight & The Wonder

Love, ambition, legacy, and the courage to build a life on your own terms.

II

Dreams are blueprints

How ideas become enterprises, and how courage and execution turn vision into legacy.

III

Raising kings

Motherhood, values and leadership — strength, wisdom and expectation in modern America.

IV

The power of partnership

Long-term love, reunion, and building a life with someone who truly knows you.

V

New Africa House

A journey back to UMass Amherst and the cultural spaces that shaped a generation.

VI

The courage to build

Women, entrepreneurship and ownership — claiming space and launching with purpose.

VII

Legacy work

Building institutions, families and communities that future generations can stand inside.

VIII

Light bearers

Leadership, vision, and the responsibility to use your gifts to lift others.

Audiences

Universities and colleges, women's leadership events, entrepreneurship conferences, arts and cultural festivals, corporate leadership programs, civic gatherings, art installations and book fairs.

New work can be commissioned to an event's theme.

Speaking fees

ProgramRange
Keynote address / major eventsUp to $20,000
Corporate & conference programsBy quote
Universities & cultural institutionsBy quote
Community & nonprofit eventsFrom $1,500

The divisions

A hospitality group that builds.

Three inns, a technology platform, a project and energy management arm, and a food and beverage line now in development.

Technology division

Get Spacii

A proprietary platform for discovering and booking event venues across Maryland, DC and Virginia — built from the operator's side of the desk.

Visit Get Spacii

Food & beverage

The Oaks Pantry

Recipes developed in our own kitchens, brought direct to consumers. Launching through the Nasdaq Milestone Circles program.

Join the launch list

Project management

Project, construction & energy

Compliance-forward project delivery and subcontractor management for public and private clients across the Mid-Atlantic.

Discuss a project

Ownership

Built by two people, together.

Sharon Jackson Wilder, Esq.

Co-founder & chief executive officer

An attorney with a background in project management, hospitality and compliance, Sharon directs corporate strategy, marketing, operating and diversity management plans for clients — and curates the group's luxury experiences and events.

A Georgetown Law graduate and nationally recognized compliance, equity and inclusion executive, she has held senior policy advisor and leadership roles at national companies, major institutions, universities and in local government. She is also the founder of Get Spacii, and a mother of four sons.

B. Quinton Wilder

Co-founder, chief operating officer & executive chef

Quinton has been part of his family's Boston catering business for more than forty years. A wine enthusiast with particular expertise in pairing wine with food and cigars, he leads the kitchen and the guest experience across all three properties.

Highly skilled in client relationship management, he brings an extensive background in non-profit higher education and health care administration to the group's operations.

In their words

What guests and audiences say.

The Weight & The Wonder journey reminds us that even while carrying history, we are still building the future.
Howard County Black Expo Poetry Slam · 2025
Not only did your team organize a great event at The Roots Fest, but Sharon delivered such powerful words in a way that all the attendees could relate to.

Plan your visit

Guides, menus and one-sheets.

Reservations & inquiries

Tell us what you're planning.

One form for every service — a stay, an event, a retreat, a consultation, a training, or a speaking engagement.

We reply to every inquiry. For same-day requests, call 202-681-4466.

The Oaks Letter

Seasonal openings, event dates, and first word when the pantry line launches.