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Bennington, VT 
Magician / Holiday Entertainment 
30 miles from Pittsfield 
19 Verified Bookings Bill D. said “Doug was great. Excellent with kids and adults at this mixed event.”
Springfield, MA
Santa Claus / Holiday Entertainment
41 miles from Pittsfield
2 Verified Bookings Keith Y. said “Santa Herb was a pleasure to work with and did a great job interacting with the kids of all ages!”
Offers Virtual Services
Monson, MA
Santa Claus / Holiday Entertainment
53 miles from Pittsfield
13 Verified Bookings Tanya H. said “Our kiddos loved their visit from Santa Ray. He had an answer for everything! Including why he was driving a car & not a sleigh. A jolly fellow and…”
Thomaston, CT
Santa Claus / Holiday Entertainment
54 miles from Pittsfield
18 Verified Bookings Stanley H. said “on time and early very nice people I would recommend very realistic”
Hartford, CT
Holiday Entertainment
56 miles from Pittsfield I am a Holiday performer with strong character skills available to emcee, walk around interaction, story-telling, etc. For adult or family events. Characters include:…
Offers Virtual Services
Coventry, CT
Santa Claus / Holiday Entertainment
66 miles from Pittsfield
8 Verified Bookings Lynne R. said “Santa was enchanting and serenaded the kids with his ukulele and sing a long. His Ho Ho Ho's were the best and his presence at our corporate kids party…”
Westbrook, CT
Children’s Music / Holiday Entertainment
90 miles from Pittsfield Shake eggs, bang on drums, twirl hula hoops, explore yoga poses, play with the world's biggest bubbles; Everyone loves this family favorite rockin' railroad band!…
Offers Virtual Services
Westport, CT
Harpist / Holiday Entertainment
91 miles from Pittsfield
32 Verified Bookings Marsha O. said “Wendy was perfect. She was most helpful with music selections and the suggestion of including a violinist with the harp. She communicated regularly and…”
Nashua, NH
Neil Diamond Tribute / Holiday Entertainment
93 miles from Pittsfield Ron has been thrilling Neil Diamond fans with his sound-alike tribute shows through-out New England for over ten years, bringing the excitement of a live Neil Diamond…
In the past year, Holiday Entertainers have sent 596 quotes to event planners
Holiday Entertainers rank #131 in popularity out of 544 categories on GigSalad
2,707 Holiday Entertainer reviews on GigSalad with an average rating of 4.9 stars
Are you planning a jolly Christmas gathering? What about a Halloween costume party? Or is it a lovey-dovey Valentine’s date that you’re trying to plan? No matter what holiday you’re celebrating, these entertainers know just how to liven up any seasonal event. Whether you’re planning a small, intimate gathering of loved ones or if you’re hosting a large corporate event, these holiday entertainers will tailor their talents so they can transport you and your guests to the North Pole for Christmas, to a haunted graveyard for Halloween, or to a romantic getaway for Valentine’s! Search for Holiday Entertainment in Pittsfield, Massachusetts above.
Please note that these Holiday Entertainment may also travel to Lanesborough, Dalton, Berkshire, Lenox, New Lebanon, Hancock, Richmond, Hinsdale, Lenox Dale, Cheshire, Washington, Washington, Becket, Stephentown, Peru, Canaan, Lee, West Stockbridge, Windsor, Stockbridge, West Lebanon, South Lee, East Chatham, Glendale, Adams, Middlefield, Austerlitz, East Nassau, Savoy, and Tyringham.
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