Swaledale Festival has received no less than six major awards in recent years, and one of its board members received an individual award for exceptional service.

In 2009 Swaledale Festival picked up its first international award: the Ability Media International Award for Inclusivity and Artistic Excellence. This was awarded for 'Semmerwater', a community play commissioned by the Festival's Artistic Director Malcolm Creese and written by composer David Gordon and author Ann Pilling. The extraordinary work featured around 100 local people aged 4 to 87. It was performed only once, in Grinton church, but it is hoped that it will surface again in the future. Some of the children who performed in the play attended the glittering awards ceremony at Kings Place in London where other winners included the BBC's Frank Gardner, the Royal College of Nursing, English National Opera and the Royal Shakespeare Company.

In 2011 the Festival received the Dalesman Magazine's Top Award for Artistic and Cultural Achievement. Malcolm Creese was presented with the award by Welcome to Yorkshire's Gary Verity at a ceremony in Skipton. 

In 2012 Swaledale Festival was named as Richmondshire District Council's Community Group of the Year, and was praised for its outstanding work in the areas of outreach and education.

In June 2014, the Festival was chosen by David Cameron to receive the much coveted Prime Minister's Big Society Award for its education and outreach work; specifically the multi-stranded Percussion Project which involved a hundred 7 to 11 year-olds making and playing their own instruments. This was Swaledale Festival's fourth major award in six years. All the children, teachers, helpers, artists, musicians and volunteers at Gayle Mill who worked so hard on the project should take credit, as should the organisations which generously funded the project: NYMAZ - North Yorkshire Youth Music Action Zone, Youth Music, the Charles and Elsie Sykes Trust, the Co-op and the Ministry of Defence.

Also in 2014, the Festival's longest-serving board member, Felicity Manning, picked up the British Arts and Science Festivals Association Award for Exceptional Service. Until her retirement in 2016, Felicity recruited and organised all of the volunteer events stewards, and she also managed the artists' accommodation and transport requirements each year.

In 2015 the Festival was one of just 16 in the UK to be awarded the new EFFE (Europe for Festivals - Festivals for Europe) label in recognition of its artistic quality, its involvement in its local community and its values of openness and inclusiveness. This scheme is supported by the EU parliament and commission. Board member Janet Hall attended the scheme's official launch and first award giving ceremony in Paris in September 2015.

In 2016 Swaledale Festival was one of just six organisations in the whole of Yorkshire to be a finalist for a Welcome to Yorkshire White Rose Award in the Arts and Culture Category. 

In 2017 Swaledale Festival was again chosen as one of a select group of UK festivals to be awarded the EEFE badge.

In 2018 the Festival received the prestigious Queen's Award for Voluntary Service - the equivalent of an MBE for volunteers! 

In 2021 Swaledale Festival was shortlisted for the Fantastic for Families Award for its Family Fun Weekend on Reeth Green.