- Silver Spring, MD
- Balloon Twister / Outdoor Party Entertainment
- 29 miles from Annapolis
- Starts at $145
Puja P. said
“Everything was awesome! ”
The 261 Best Outdoor Party Entertainers for hire in Annapolis, MD
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409 Outdoor Party Entertainers serving Annapolis, MD
- Washington, DC
- Fire Performer / Outdoor Party Entertainment
- 30 miles from Annapolis
- Starts at $850
Lori B. said
“They were very friendly and great with large crowd. ”
- Washington, DC
- Fire Performer / Outdoor Party Entertainment
- 30 miles from Annapolis
- Starts at $400
Ebony B. said
““Honestly, the fire show was EVERYTHING! It gave the party that unexpected, elevated wow factor and made Robin's celebration feel like a true VIP experience. Moses was incredibly professional,... ”
Zelan-Juggler
1 Verified booking- Greenbelt, MD
- Juggler / Outdoor Party Entertainment
- 21 miles from Annapolis
- $500 – $2,000 per event
Juggling, Unicycle, Stilt walking, Shape Spinning, Fire-Juggling
- Baltimore, MD
- Fire Performer / Outdoor Party Entertainment
- 22 miles from Annapolis
- Starts at $1,000 per hour
Elizabeth A. said
“wonderful performance and amazing to work with! ”
- Washington, DC
- Fire Performer / Outdoor Party Entertainment
- 30 miles from Annapolis
- Contact for pricing
Anastasia F. said
“Breathtaking performance at an Open Mic event at FaceClock Gallery! She is so talented and we will book her again for our next event without a doubt! ”
- Washington, DC
- Fire Performer / Outdoor Party Entertainment
- 30 miles from Annapolis
- Contact for pricing
Michele D. said
“Our performer was great. She was on time, had a great personality, and was very flexible with our plans and timings. Would for sure use them again and recommend them to anyone looking for unique... ”
- Towson, MD
- Reptile Show / Outdoor Party Entertainment
- 30 miles from Annapolis
- $195 – $695 per event
Dana H. said
“Great experience for the kids! Was able to ask and answer questions while holding the animals that were brought along. Will be booking again for future camp. ”
- Glen Burnie, MD
- Fire Performer / Outdoor Party Entertainment
- 15 miles from Annapolis
- Contact for pricing
Tamara G. said
“Hoopsista captured the crowd with her elite fire dance performance the crowd was in awww and excited the entire show. I would definitely book her again ”
- Silver Spring, MD
- Balloon Twister / Outdoor Party Entertainment
- 29 miles from Annapolis
- Contact for pricing
Obha O. said
“Thank you Stripes for being so amenable and transparent with communication! ”
DJ Shama
- Washington, DC
- Mobile DJ / Outdoor Party Entertainment
- 30 miles from Annapolis
- $125 per hour
Aldo T. said
“Dj Shama was booked for a surprised birthday party, and he rocked the party. He was very professional with great attitude and personality. He arrived early and was well prepared. His music selection... ”
Whimsical Expressions
New member- Annandale, VA
- Face Painter / Outdoor Party Entertainment
- 39 miles from Annapolis
- Contact for pricing
I've created Whimsical Expressions Face & body painting to add color to the lives of individuals, or an event. I want to encourage and create a magical space...
- Hanover, MD
- Face Painter / Outdoor Party Entertainment
- 19 miles from Annapolis
- $125 per event
Aasma R. said
“Huge shoutout to @moondust face art! Her work is amazing and she’s wonderful with guests. The kids gave her 11/10 stars—we couldn’t have asked for a better artist for our party. Highly recommend!!! ”
- Lanham, MD
- Mobile DJ / Outdoor Party Entertainment
- 20 miles from Annapolis
- Starts at $950
Jay D. said
“DJ Kelly Kellz is a phenomenal DJ! She listens to her clients wants & curates music & a vibe that exceeds their expectations! She's my go-to DJ for all of my events & is extremely professional,... ”
- Beltsville, MD
- Concessions / Outdoor Party Entertainment
- 23 miles from Annapolis
- $150 per event
Anna K. said
“Hired her for my niece’s birthday party oh boy, she was a gem! She is definitely a one stop concession stand. Communication was on point, everything was organized, and the guests absolutely loved... ”
- Catonsville, MD
- Stilt Walker / Outdoor Party Entertainment
- 24 miles from Annapolis
- Starts at $200
Emily P. said
“Melissa was great! At our senior living community, we held a car show and Melissa was the perfect addition to add some entertainment throughout the parking lot! She was great with the kids and... ”
- Windsor Mill, MD
- Face Painter / Outdoor Party Entertainment
- 28 miles from Annapolis
- Starts at $100
Ruchel C. said
“Lora was incredibly accommodating with her time, especially as we had more children interested in face painting than anticipated. She was a pleasure to work with and was a wonderful addition to our... ”
- Washington, DC
- Balloon Twister / Outdoor Party Entertainment
- 30 miles from Annapolis
- Contact for pricing
Loretta G. said
“Happy customers at our National Night Out event. The line was well paced, balloons were great, and Arabella was pleasant to work with. Very much recommend. ”
- Washington, DC
- Fire Performer / Outdoor Party Entertainment
- 30 miles from Annapolis
- Starts at $400
Kim C. said
“Sha was awesome! Punctual, polite, professional and really wowed the crowd!! ”
- Alexandria, VA
- Face Painter / Outdoor Party Entertainment
- 32 miles from Annapolis
- $100 – $155 per event
Lizbeth H. said
“We had such a great painter. She was fast and also great with the students at our school's spring festival! Will be booking for future events! ”
- Fort Belvoir, VA
- Face Painter / Outdoor Party Entertainment
- 40 miles from Annapolis
- Starts at $150 per hour
Stephanie H. said
“Lindsey was amazing! Arrived early, fully prepared and ready to go. Worked so well with so many kids. Her creativity and artistry were fantastic! Thanks for making our event a success! ”
Enchanted Party Arts
1 Verified booking- Severna Park, MD
- Face Painter / Outdoor Party Entertainment
- 7 miles from Annapolis
- Starts at $100
Anna is a professional face painter who brings imagination, color, and excitement to every event. With a passion for art and a talent for creating...
- Crofton, MD
- Balloon Twister / Outdoor Party Entertainment
- 11 miles from Annapolis
- Starts at $150
Jamie D. said
“We really enjoyed having Sarah! She was communicative before the event, showed up on time, and cleaned up after her shift. The kids all enjoyed the range of balloon creations, although most wanted... ”
- Severn, MD
- Mobile DJ / Outdoor Party Entertainment
- 16 miles from Annapolis
- Starts at $125 per hour
April L. said
“We had a great Employee Appreciation Day thanks to DJ Rome! We have a very diverse staff demographic so we needed a wide variety of music ranging from r&b, soul, Spanish, and county. He was able to... ”
- Upper Marlboro, MD
- Mobile DJ / Outdoor Party Entertainment
- 18 miles from Annapolis
- $600 – $2,000 per event
Kim V. said
“Adrian (DJ Prez) surpassed my expectations for a wedding DJ. He arrived to the venue early for set up, was attentive in following up and sorting out details ahead of time, respectful, courteous, and... ”
- Laurel, MD
- Mobile DJ / Outdoor Party Entertainment
- 21 miles from Annapolis
- $400 – $2,000 per event
Ashley J. said
“The best thing my fiancé and I could have added to our engagement party was a DJ, and DJ Sha The Goddess was the perfect pick! She made the entire process, from booking to preparing for setup for... ”
- Baltimore, MD
- Face Painter / Outdoor Party Entertainment
- 22 miles from Annapolis
- $75 – $500 per event
Frederick H. said
“Our face painter showed up early to get set up and she was all set to go at the designated time. She was so friendly and very talented! ”
- Baltimore, MD
- Mobile DJ / Outdoor Party Entertainment
- 22 miles from Annapolis
- Starts at $350
Toni F. said
“Dj Vickzen was the dj for my birthday this year and i look forward to booking her next year as well! Every guest just loved her ”
- Baltimore, MD
- Stilt Walker / Outdoor Party Entertainment
- 22 miles from Annapolis
- Contact for pricing
Melissa J. said
“Kris was a fun addition to our "float" for the Annapolis St Patrick's Day Parade. Kris was professional, dressed the part as a leprechaun, and walked 1.5 miles without an issue. I would definitely... ”
THE MUSICOLOGIST Professional Music Entertainment Services
1 Verified booking- Baltimore, MD
- Mobile DJ / Outdoor Party Entertainment
- 22 miles from Annapolis
- Starts at $400
We pride ourselves with offering the very best sound systems, studio quality wireless microphones and a vast music library of many genres catering to a wide...
- Baltimore, MD
- Reptile Show / Outdoor Party Entertainment
- 22 miles from Annapolis
- $200 – $300 per event
Bianca A. said
“I made the bold move of hiring a snake show for my daughter's second birthday. Honestly, it was the best decision ever made!!! The snakes were a HUGE HIT!!! They were so gentle, and beautiful. It... ”
- Baltimore, MD
- Juggler / Outdoor Party Entertainment
- 22 miles from Annapolis
- Contact for pricing
Doug S. said
“Super great, especially interacting with kids, but adults too. Loved the show stopping big ending. Great job! ”
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About booking Outdoor Party Entertainment in Annapolis, MD
Outdoor parties are all about enjoying fun in the sun and creating an atmosphere guests won’t forget. The right entertainment sets the stage, whether that means a live band filling the air with music, a DJ keeping the energy high, or a magician amazing guests with close-up tricks. From stilt walkers and petting zoos to face painters and balloon twisters, professional entertainment brings the spark that transforms any backyard celebration, kids party, or festival into an unforgettable experience.
The cost of hiring outdoor party entertainers in Annapolis, Maryland will vary depending on the type of act, their experience, and the length of the performance. For example, a strolling juggler for a few hours will cost less than a full band or stage show. Contact the local entertainers above to discuss your event details and receive a customized quote.
As you browse Annapolis outdoor party entertainers, check out their profiles to learn about their services, browse photos, and watch promotional videos. Then, read over reviews from past clients to see how they’ve entertained at similar events. When requesting a quote, include key details such as your event location, audience size, performance space, and overall vibe to get the most accurate pricing.
Once you find the entertainer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book outdoor party entertainment. You can message the performers, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just sit back and enjoy your party!
Outdoor Party Entertainment serving the Annapolis, MD area
These Outdoor Party Entertainment serve the wider Annapolis and Anne Arundel county area and travel to Parole, Arnold, Foxmoor, Edgewater, Riva, Mayo, Herald Harbor, Crownsville, Severna Park, Gibson Island, Davidsonville, Arden on the Severn, Lake Shore, Shady Side, Stevensville, Galesville, Pasadena, Millersville, Harwood, West River, Crofton, Chester, Gambrills, Lothian, Churchton, Riviera Beach, Odenton, Deale, Glen Burnie, and Tracys Landing.