Good morning, Portland.

Skateboarders took over Exchange Street on Sunday for the first Cobble to Cobble block party held by Mocean Skateboards and the Old Port Company, featuring art, music, fashion and a trick contest with a $3,000 cash prize—sponsors included Red Bull and New Balance.

Community meals will be offered in Buxton, Gorham, Gray and Westbrook from Oct.

4 to Oct. 18. Events include bean suppers, a drive-thru turkey dinner and a free weekly meal at local centers—prices range from $10 to $12 with discounts for children.

Wayside Food Programs will host its annual fundraiser Inside Wayside on Thursday at 135 Walton Street in Portland to help fight hunger in Maine — tickets cost $60 and the event will include live music, an auction and more.

Abstract artist Richard Keen from Surry discussed his work using shadow and color to show Maine’s underwater coast at Pineland Farms’ Unity Environmental University in New Gloucester last Thursday—drawing on his experience as a diver.

Ricker Hill Orchards in Turner has faced a severe drought that made its apples smaller and reduced pick-your-own sales, and owners Jeff Timberlake and Jenny Maaheu worry that stressed trees may yield fewer apples next year+ they plan to adjust their production if dry conditions continue.

At a Monday meeting in Portland, activists challenged the jail’s agreement to hold ICE detainees while county commissioners admitted they were unclear about state law that requires the facility to house federal inmates.

Sheriff Kevin Joyce said the jail held 63 ICE detainees and the federal contract brings in funds—critics argue this setup may enable practices that have sparked local fears.

Federal workers and Mainers who depend on federal services face uncertainty as a government shutdown looms, with possible delays in food stamp payments and new benefit applications and potential furloughs for some civil workers while essential operations like military work and air traffic control continue. A state law offers no interest loans to federal and state workers who may lose pay, and agencies will review plans to limit disruptions—local courts and park services could be affected if a shutdown occurs.

Maine's Cooper Flagg was seen shaking hands with Michael Jordan at the Ryder Cup golf tournament in New York on Saturday—ESPN named him one of the top 100 NBA players for the 2024-2025 season.

He had fun at a fair with teammate Dereck Lively the day before.

Fiction Workshop

10:30 p.m. – 12:30 a.m. — 105 St James St, Portland, ME — Cost not specified — Connect with fellow writers and enhance your fiction writing skills in this engaging workshop.

Scenic Train Ride

10 a.m. — Maine Narrow Gauge Railroad — $0 to $23.50 — Enjoy a scenic 40-minute train ride with beautiful views of Casco Bay and learn about Maine's narrow gauge railroading history.

The California Honeydrops Concert

7-9 p.m. — State Theatre — Ticket information available — Experience the vibrant sound of The California Honeydrops on their Redwood Highway Tour.

Scenic Train Ride

11 a.m. — Maine Narrow Gauge Railroad — $0 to $23.50 — Experience a charming 40-minute train ride along the stunning Casco Bay while uncovering the history of narrow gauge railroading.

Scenic Train Ride in Casco Bay

10 a.m. — Maine Narrow Gauge Railroad — $0 to $23.50 — Experience a nostalgic 40-minute train ride with stunning waterside views and rich history.

Mainebiz Portland 60 Ideas in 60 Minutes Forum 2025

7:30-10:30 a.m. — DoubleTree by Hilton Hotel Portland — Ticket prices vary — Gain 60 actionable business ideas from Maine CEOs to inspire your career.

Scenic Train Ride

10 a.m. — Maine Narrow Gauge Railroad — $0 to $23.50 — Experience a 40-minute scenic train ride along Casco Bay while learning about Maine's rich railroading history.

Fall Foliage Wine Sail in Portland, Maine

3-5 p.m. — Maine State Pier — $150 — Experience a scenic sail through Casco Bay while enjoying exquisite European wines and autumn vistas.

LYRES! Concert with Mal Thursday and Tiger Bomb

7-11 p.m. — Veterans of Foreign Wars — Tickets available — Experience Boston's garage revival legends LYRES live in Portland alongside local acts Mal Thursday and Tiger Bomb.

Fall Foliage Champagne and Oysters Sail

3-5 p.m. — Maine State Pier — $195 — Sail through scenic Casco Bay while enjoying exquisite Champagnes and fresh oysters.