 "It's the Grand Pumpkin, Milhouse" was regarded by reviewers as the best segment in the episode. Canning wrote, "this segment may not be all that gory, but it's funny and, quite honestly, it will just make you feel good", and Bentley described it as "a dead-on comedy assault of the Charlie Brown animated Halloween special." Rob Owen of the Pittsburgh Post-Gazette concurred, writing that it "succeeds because it offers sly cultural commentary." Show Patrol wrote "The nostalgia factor makes “ Grand Pumpkin ” the best of these amusing bits for me, but they all lack that trademark “ Simpsons ” brand of satirical smartness." Hal Boedecker of the Orlando Sentinel gave the episode a 4 / 5 and called the final segment a "witty parody of Charlie Brown's Halloween classic. [...] The best gag, though, is a subtle one. Marge plays a trombone, a loving salute to the way the Peanuts specials portrayed adult voices."
