The reaction of 7-methoxy-benzofuran-2-carboxylic acid hydrazide (2) with acetic anhydride gave the acetyl derivative 3, which underwent cyclisation by treatment with POCl3 yielded 4, with ethylchloroformate in methanol yielded 5 and with ethylchloroformate in dry benzene followed by POCl3 cyclisation resulted into 7 via the compound 6. On the other hand, the reaction of 2 with acetyl acetone, benzoyl acetone, and ethylacetoacetate resulted into pyrazoles 8, 9 and 10 respectively. All the new heterocycles have been characterized by elemental analysis, IR, 1H-NMR and GCMS spectral data. Further, these have been screened for antimicrobial, antioxidant, analgesic, anti-inflammatory and antipyretic activities. Compounds 5 and 7 exhibited encouraging results and remaining exhibited moderate activity.