Fall-o-Ween at Frog Pond

Mayor Michelle Wu and the Boston Parks and Recreation Department will host the sixth annual Fall-o-Ween Children’s Festival at the Boston Common Frog Pond. The Fall-o-Ween Children’s Festival is presented by the Boston Parks and Recreation Department in partnership with the Skating Club of Boston. The key sponsors are Raising Cane’s Chicken Fingers and HP Hood LLC. Additional support is provided by New England Dairy Council. Adults and children are encouraged to wear Halloween costumes and participate in a wide range of free, fun, and spooky family-friendly activities. Test your speed in our Monster Dash Obstacle Course or Alpine Slide and try the Jumpin’ Pumpkin or Scarecrow Slide. A “monster mash” of activities will include music, arts and crafts, treats, and field games facilitated by Knucklebones. Visit the New England Dairy displays to enjoy both the Mobile Dairy Bar and the Mobile Dairy Experience.  Enjoy live entertainment at the Parks Department Stage with music and magic! This family friendly event takes place on Friday, October 16th from 4pm-8pm at the corner of Charles and Beacon Street. 

The great outdoors – Outdoor dining extended to November 15

Good news if you’re not ready to say goodbye to patio season just yet! The City of Boston has extended its 2026 Outdoor Dining season through November 15th, giving restaurants a couple more weeks to keep the tables and chairs outside. Restaurants participating in the program can continue outdoor dining, weather permitting. The City reminds businesses not to use outdoor setups during inclement weather or when snow is on the ground. The extension also applies to Boston’s Food Truck Program, allowing participating food trucks to continue operating at their approved locations through November 15th. So, grab that sweater and enjoy a few more meals and drinks outside before winter officially takes over! An interactive map of restaurants with outdoor dining can be found here.

Pasta on the Pier

Good news for pasta lovers! Pasta on the Pier is back at Reel House. Every Thursday, enjoy a four-course dinner for just $30, featuring fresh, locally made pasta from Lilly’s. Gluten-free options are available, too! So, if you’re looking for an easy Thursday night dinner plan, this is it. Make a reservation and bring your appetite!

Sweater Weather Takes over City Hall Plaza

 Sweater Weather Fest, the first film festival to be held on Boston City Hall Plaza, will take place Saturday, Oct. 17, 2026, from 2 p.m. until 11 p.m. Free and open to all ages, the outdoor festival will feature industry panels, film screenings, DJs, local food and vendors, and activities connecting attendees with Massachusetts’ film and television community. The evening will close with the final two episodes of Apple TV’s “Widow’s Bay,” projected onto the festival’s giant 60-foot screen on the plaza. Filmed in Massachusetts, including Gloucester and Rockport, the horror-comedy series recently won 14 Emmy Awards, including outstanding comedy series, becoming the most awarded first-season comedy in Emmy history.  Get all the details here.

Noche de Catrinas Mexican Celebration in Eastie

Celebrate Mexican culture and traditions at the Noche de Catrinas Mexican Celebration on Saturday, October 17th, from 5:30pm–11pm at the Veronica Robles Cultural Center, 282 Meridian Street! This free event will feature live music, dance performances, traditional art, and delicious Mexican food and drinks available for purchase. A fun night of culture, community, and celebration! Get all the details here.

Have a wonderful week! Thank you to our Caught in Eastie readers and Neighborhood Partners for supporting our local journalism efforts!