A study on multipass harvesting using a mechanical harvesting prototype was proposed for mechanical harvesting of fresh market sweet cherries. Fruit damage rate, fruit removal rate, and fruit maturity level were three of the measures used to compare the performance of the multipass harvesting method against single-pass harvesting. The multipass harvesting was conducted in four consecutive days with short duration of 2.5 seconds at each day, while the single-pass harvesting was one-time harvesting with long duration of 10 seconds at a single day. To generate baseline information for comparison, single-pass harvestings were performed on the first and the last days of the multipass harvesting. Fruit maturity level was determined by comparing the fruit skin color against a standard color chart with seven color levels. Field test results showed that the percentage of under-mature fruit (maturity levels ≤ 5) was substantially lower with multipass harvesting than that with day 1 single-pass harvesting. Similarly, the percentage of over-mature fruit (maturity level 7) was noticeably lower with multipass harvesting than that with day 4 single-pass harvesting. Multipass harvesting achieved a fruit removal rate of 83.4% ± 10.3% and a harvest-induced fruit damage rate of 5.0% ± 4.4%. The corresponding fruit removal rates from single-pass harvesting tests were 48.0% ± 16.1% on day 1 and 66.7% ± 16.2% day 4. Harvest-induced fruit damage rates with single-pass harvesting were 20.1% ± 9.9% on day 1 and 11.8% ± 6.0% on day 4. The results supported the hypothesis that multipass of short-duration shaking offer a potential to achieve a higher overall harvesting efficiency with better fruit quality, and therefore could lead to an optimal solution for mechanical harvesting of fresh market sweet cherries. It is noted that comprehensive economic analysis will be necessary to establish commercial viability of the system in comparison with single-pass solutions.