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Grief counselors and therapists in Boston, MA


Top grief and loss counseling therapists in Boston, MA
Grieving in Boston doesn't mean grieving alone. Headway connects you with warm, empathetic providers trained in meaning-making and trauma-informed grief work across neighborhoods like Back Bay, Dorchester, and Jamaica Plain. Sessions are available as soon as tomorrow with copay estimates as low as $0 through insurance.
We all need connection, community, and the ability to be our authentic selves in order to thrive. Many of us are not provided these attachment needs in childhood, and we grow into adulthood burdened by this wounding, unsure of how to relate safely and from a place of wholeness. If you struggle to align your inner and outer worlds, find yourself repeating difficult relational patterns, or feel as if your authentic self must remain hidden, I would love to work with you. I am particularly interested in supporting the health of queer families and cooperatives.
As a licensed substance use and addiction counselor, I believe that recovery is not a one-size-fits-all journey—it’s a deeply personal process that deserves compassion, respect, and hope. Every individual’s story is unique, and so are the reasons behind their struggles with substance use. My approach is rooted in the belief that healing happens when people feel truly seen, heard, and supported without judgment. I view my role not as someone who tells clients what recovery “should” look like, but as a guide who helps them discover what recovery means for them.
Framingham State University- BS (Bachelor of Science)
Springfield College- MSW (Masters of Social Work)
LICSW (Licensed Independent Clinical Social Work)
With over 15 years of experience, I believe in considering the unique perspectives and experiences of each individual and tailoring the counseling process to your needs and context.
For over 30 years, I have assisted individuals navigate significant transitions and emotional struggles. Since 2007, I have been certified in hypnotherapy after completing 10 years of study in clinical hypnosis along with training in Systems Theory, psychodynamic psychotherapy, Internal Family Systems IFS), mindfulness, and spirituality without religious affiliation.
Many people come to therapy feeling overwhelmed by anxiety, trauma, relationship challenges, or life experiences that have left them feeling disconnected from themselves or uncertain about how to move forward. I believe that healing begins with feeling truly seen, heard, and accepted. I am passionate about helping clients recognize their strengths, reconnect with their authentic selves, and build lives that feel more grounded, meaningful, and aligned with who they are.
I earned my Master's degree from Springfield College in 2007 and bring nearly two decades of clinical experience across a wide range of settings, including outpatient clinics, in-home therapy, residential treatment, juvenile justice programs, school-based services, and as a school adjustment counselor. These experiences have given me a deep understanding of how trauma, relationships, and life experiences shape emotional well-being across the lifespan. While my background includes extensive work with children, adolescents, and families, my practice is primarily focused on supporting teens and adults who are navigating life's challenges. I am committed to providing culturally responsive, affirming care that honors each person's unique identity and lived experience.
Amy Penny is a passionate and dedicated therapist who believes that every person holds limitless potential and inner strength waiting to be discovered. Drawing from her own experiences of overcoming adversity and her clinical expertise, Amy creates a safe and supportive space where individuals feel empowered to connect with their inner resources and move toward growth and healing.
About our therapists located within 20 miles of Boston, MA who help people navigate grief and loss



- 100%Anxiety
- 100%Grief or loss
- 95%Depression
- 90%Stress management
- 88%Trauma

- 98%Aetna
- 83%Harvard Pilgrim Healthcare
- 73%Cigna
- 68%Carelon Behavioral Health
- 55%Blue Cross Blue Shield of Massachusetts

- 98%English
- 8%Igbo
- 5%Portuguese
- 5%Spanish
- 3%Haitian Creole

- 95%In-person or online
- 5%In-person only

- 65%Woman
- 33%Man
- 3%Non-binary

- 30%Advanced Practice Registered Nurse
- 30%Licensed Mental Health Counselor
- 28%Licensed Independent Clinical Social Worker
- 5%Clinical Psychologist

- 98%Individual therapy
- 20%Family therapy
- 10%Child or adolescent therapy
- 5%Couples therapy
Frequently asked questions


Find the right grief counselor for you
Headway makes it easy to find a therapist who can support you through loss — from finding the right provider, to understanding costs, to scheduling with ease.
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