--- title: "Annapolis events this week: Pumpkin Walk, Naptown Flea Halloween Night Market and more" description: "Things to do in Annapolis this week, Oct. 27 to Nov. 2, 2026: Pumpkin Walk; Naptown Flea Halloween Night Market; Halloween Concert." image: https://blog.evvnt.com/hubfs/evvnt-blog/cityevents-20261026/annapolis-events-this-week-oct-27-nov-2-2026-header.jpeg --- [Skip to content](https://blog.evvnt.com/local/annapolis-events-this-week-oct-27-nov-2-2026#main-content) [![Evvnt](https://blog.evvnt.com/hubfs/Evvnt_Rework_Final-01%20(1)-2.svg "Evvnt")](http://www.evvnt.com) Search # Annapolis events this week: Pumpkin Walk, Naptown Flea Halloween Night Market and more [J.A.R.V.I.S .](https://blog.evvnt.com/local/author/jarvis) Oct 26, 2026, 5:54:00 PM ![Evvnt blog](https://blog.evvnt.com/hs-fs/hubfs/evvnt-blog/cityevents-20261026/annapolis-events-this-week-oct-27-nov-2-2026-header.jpeg?width=1200&name=annapolis-events-this-week-oct-27-nov-2-2026-header.jpeg) Share - [fFacebook](https://www.facebook.com/sharer/sharer.php?u=https%3A%2F%2Fblog.evvnt.com%2Flocal%2Fannapolis-events-this-week-oct-27-nov-2-2026) - [ùïèX](https://twitter.com/intent/tweet?text=Annapolis+events+this+week%3A+Pumpkin+Walk%2C+Naptown+Flea+Halloween+Night+Market+and+more&url=https%3A%2F%2Fblog.evvnt.com%2Flocal%2Fannapolis-events-this-week-oct-27-nov-2-2026) - [inLinkedIn](https://www.linkedin.com/sharing/share-offsite/?url=https%3A%2F%2Fblog.evvnt.com%2Flocal%2Fannapolis-events-this-week-oct-27-nov-2-2026) - [WhatsApp](https://wa.me/?text=Annapolis+events+this+week%3A+Pumpkin+Walk%2C+Naptown+Flea+Halloween+Night+Market+and+more+https%3A%2F%2Fblog.evvnt.com%2Flocal%2Fannapolis-events-this-week-oct-27-nov-2-2026) - [Messenger](fb-messenger://share/?link=https%3A%2F%2Fblog.evvnt.com%2Flocal%2Fannapolis-events-this-week-oct-27-nov-2-2026) - [‚úâEmail](mailto:?subject=Annapolis+events+this+week%3A+Pumpkin+Walk%2C+Naptown+Flea+Halloween+Night+Market+and+more&body=Things+to+do+in+Annapolis+this+week%2C+Oct.+27+to+Nov.+2%2C+2026%3A+Pumpkin+Walk%3B+Naptown+Flea+Halloween+Night+Market%3B+Halloween+Concert.%0A%0Ahttps%3A%2F%2Fblog.evvnt.com%2Flocal%2Fannapolis-events-this-week-oct-27-nov-2-2026) - üîóCopy link Follow Evvnt - [YouTube](https://www.youtube.com/channel/UCrMM_e9d4Nwx5uNMvs19KVA) - [TikTok](https://www.tiktok.com/@evvnt) - [Instagram](https://www.instagram.com/evvnt/) Halloween falls on a Saturday this year, and Annapolis has a full weekend of things to do. Here are 4 events happening this week, Oct. 27 to Nov. 2. ## 1. Pumpkin Walk **When:** Friday, Oct. 30, 4 to 6 p.m. **Where:** Hammond-Harwood House Crafts, storytelling, face painting and a costume parade; $25 per family. [Event details](https://hammondharwoodhouse.org/event/pumpkin-walk-2026/). ## 2. Naptown Flea Halloween Night Market **When:** Friday, Oct. 30, 5 to 10 p.m. **Where:** GameOn A Halloween night market. [Event details](https://www.eventbrite.com/e/naptown-flea-halloween-night-market-tickets-2003486527135). ## 3. Halloween Concert **When:** Friday, Oct. 30, 7 and 10 p.m. and Saturday, Oct. 31, 7 p.m. **Where:** U.S. Naval Academy Chapel The Academy's Halloween/All Saints' Day concert; $40, children 11 and under $10. [Event details](https://www.usna.edu/PAO/events/2026/10/Halloween_Concert.php). ## 4. The Legend of Sleepy Hollow **When:** Saturday, Oct. 31, 8 p.m. **Where:** Colonial Players Theater The Colonial Players stage the Halloween tale. 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