If you are looking for inexpensive or free things to do in Southern Maine, you're in the right place! Here are our picks for affordable events and deals in York and Cumberland counties.
Wednesday, December 17, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Self-Guided Museum Tours | 10:00 am to 4:30 pm | FREE | Shaker Village at Sabbathday Lake, New Gloucester |
| Creative Movement with Portland School of Ballet | 11:00 am to 11:30 am | FREE | Portland Public Library, Downtown Branch |
| Kids Weekly Storytime | 11:00 am to 12:00 pm | FREE | Barnes and Noble South Portland |
| Kids' Wednesday Story Time at Barnes and Noble South Portland | 11:00 am to 12:00 pm | FREE | Barnes and Noble South Portland |
| Wells Farmers' Market | 1:30 pm to 5:00 pm | Wells Public Library | |
| Live Music at the Front Porch | 4:00 pm to 11:55 pm | The Front Porch in Ogunquit | |
| Ice Cream Night at the Trolley Museum | 5:30 pm to 7:30 pm | $12.00 | Seashore Trolley Museum |
| Wednesday Mah Jongg in Kennebunk | 5:30 pm to 7:30 pm | FREE | Kennebunk Free Library |
| Raise the Bar Trivia at Bissell Brothers Brewery in Portland | 6:00 pm to 8:00 pm | FREE | Bissell Brothers Brewery Portland |
| Best Worst Trivia at Salt Yard Cafe in Portland | 6:00 pm to 8:00 pm | FREE | Salt Yard Cafe |
| Trivia at Brickyard Hollow Brunswick | 6:00 pm to 8:00 pm | FREE | Brickyard Hollow Brunswick |
| Best Worst Trivia at Mast Landing SoPo | 6:00 pm to 8:00 pm | FREE | Mast Landing Brewing Company |
| Trivia | 6:30 pm to 7:30 pm | FREE | Kennebunk Free Library |
| Irish Music at Feile | 6:30 pm | Feile Irish Pub in Wells | |
| Best Worst Trivia at Wilson County Barbecue in Portland | 7:00 pm to 9:00 pm | FREE | Wilson County Barbecue |
| Best Worst Trivia at Smoked Portland | 7:00 pm to 9:00 pm | FREE | Smoked Portland |
| Little Shop of Horrors | 8:00 pm | $50.00-160.00 | Ogunquit Playhouse |
| Dueing Divas | 8:00 pm | $25.00 | Mainestreet |
Thursday, December 18, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Self-Guided Museum Tours | 10:00 am to 4:30 pm | FREE | Shaker Village at Sabbathday Lake, New Gloucester |
| Story Time at the Freeport Community Library | 10:15 am to 10:30 am | FREE | Freeport Community Library |
| Creative Movement with Portland School of Ballet | 11:00 am to 11:30 am | FREE | Portland Public Library, Downtown Branch |
| Crafty Kids at the Wells Public Library | 3:00 pm | FREE | Wells Public Library |
| Yarmouth Farmers' Market (May-Oct) | 3:00 pm to 6:00 pm | Bickford Pavillion | |
| Summer Sunsets Live! | 4:00 pm to 8:30 pm | FREE | Thompson’s Point |
| Live Music at the Front Porch | 4:00 pm to 11:55 pm | The Front Porch in Ogunquit | |
| Live Music at the Bitter End | 5:00 pm to 8:00 pm | The Bitter End in Wells | |
| Romance Book Club at Barnes and Noble | 6:00 pm to 7:00 pm | FREE | Barnes and Noble South Portland |
| Best Worst Trivia at Locally Sauced in Yarmouth | 6:00 pm to 8:00 pm | FREE | Locally Sauced in Yarmouth |
| Trivia at Brickyard Hollow Biddeford | 6:00 pm to 8:00 pm | FREE | Brickyard Hollow Biddeford |
| Trivia at Brickyard Hollow Ogunquit | 6:00 pm to 8:00 pm | FREE | Brickyard Hollow Ogunquit |
| Trivia at Brickyard Hollow Yarmouth | 6:30 pm to 8:30 pm | FREE | Brickyard Hollow Yarmouth |
| Trivia at Brickyard Hollow New Gloucester | 6:30 pm to 8:30 pm | FREE | Brickyard Hollow New Gloucester |
| Raise the Bar Trivia at Feile | 7:00 pm to 9:00 pm | FREE | Feile Irish Pub in Wells |
| Best Worst Trivia at Tomaso's Pizza & Burger Bar in Portland | 7:00 pm to 9:00 pm | FREE | Tomaso’s Pizza & Burger Bar |
| Best Worst Trivia at Arcadia Portland | 7:00 pm to 9:00 pm | FREE | Arcadia Portland |
| Trivia at Brickyard Hollow Portland | 7:00 pm to 9:00 pm | FREE | Brickyard Hollow Portland |
| Little Shop of Horrors | 8:00 pm | $50.00-160.00 | Ogunquit Playhouse |
Friday, December 19, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Brunswick Farmers' Market | 8:00 am to 1:00 pm | Lower Mall on Maine Street | |
| Fiber Arts for Adults at The Wells Public Library | 10:00 am to 12:15 pm | FREE | Wells Public Library |
| Self-Guided Museum Tours | 10:00 am to 4:30 pm | FREE | Shaker Village at Sabbathday Lake, New Gloucester |
| Creative Movement with Portland School of Ballet | 11:00 am to 11:30 am | FREE | Portland Public Library, Downtown Branch |
| Free Friday | 4:00 pm to 8:00 pm | FREE | Portland Museum of Art |
| Live Music at the Front Porch | 4:00 pm to 11:55 pm | The Front Porch in Ogunquit | |
| Live Music at the Bitter End | 5:00 pm to 8:00 pm | The Bitter End in Wells | |
| Karaoke at Feile | 7:30 pm to 11:30 pm | Feile Irish Pub in Wells | |
| Dueing Divas | 8:00 pm | $25.00 | Mainestreet |
| Karaoke Queen | 9:00 pm | Mainestreet |
Saturday, December 20, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Bridgton Farmers' Market | 8:00 am to 12:00 pm | Bridgton Community Center | |
| Saco Farmers' Market | 8:00 am to 12:00 pm | Saco Valley Shopping Center | |
| Sanford Farmers' Market | 8:00 am to 12:00 pm | Central Park, Sanford | |
| Kennebunk Farmer's Market | 8:00 am to 12:30 pm | Garden Street Parking Lot | |
| Gorham Farmers' Market | 8:30 am to 12:30 pm | Gorham Municipal Center | |
| Windham Farmers Market | 8:30 am to 12:30 pm | Turning Leaf Drive, Windham | |
| York Gateway Farmers' Market | 9:00 am to 1:00 pm | York Region Chamber of Commerce Visitor Center | |
| Steep Falls Farmers' Market | 9:00 am to 2:00 pm | Steep Falls Village Park Gazebo | |
| Cumberland Farmers' Market | 10:00 am to 1:00 pm | Cumberland Town Hall | |
| Self-Guided Museum Tours | 10:00 am to 4:30 pm | FREE | Shaker Village at Sabbathday Lake, New Gloucester |
| Creative Movement with Portland School of Ballet | 11:00 am to 11:30 am | FREE | Portland Public Library, Downtown Branch |
| Kids' Saturday Story Time at Barnes and Noble South Portland | 11:00 am to 12:00 pm | FREE | Barnes and Noble South Portland |
| Artsy Afternoon | 1:00 pm to 3:00 pm | FREE | South Portland Library |
| Live Music at the Front Porch | 2:00 pm to 11:55 pm | The Front Porch in Ogunquit | |
| Live Music at the Bitter End | 5:00 pm to 8:00 pm | The Bitter End in Wells | |
| Raise the Bar Trivia at Shipyard Brewpub in Eliot | 7:00 pm | FREE | Shipyard Brewpub Eliot |
| Live Music at Feile | 7:30 pm to 11:30 pm | Feile Irish Pub in Wells | |
| Little Shop of Horrors | 8:00 pm | $50.00-160.00 | Ogunquit Playhouse |
| Dueing Divas | 8:00 pm | $25.00 | Mainestreet |
| Brunswick-Topsham Land Trust Farmers’ Market | 8:30 pm to 12:30 pm | Crystal Spring Farm | |
| Dueling Divias | 9:30 pm | $25.00 | Mainestreet |
Sunday, December 21, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Scarborough Farmers' Market | 9:00 am to 1:00 pm | Scarborough Town Hall | |
| South Portland Winter Farmers' Market | 10:00 am to 2:00 pm | South Portland City Planning and Development Offices Building | |
| Gray Village Farmers' Market | 10:00 am to 1:00 pm | The Village Green, Gray | |
| Kittery Community Market | 10:00 am to 2:00 pm | Post Office Square, Kittery | |
| South Portland Summer Farmers' Market | 10:00 am to 2:00 pm | South Portland Town Office | |
| Creative Movement with Portland School of Ballet | 11:00 am to 11:30 am | FREE | Portland Public Library, Downtown Branch |
| Live Music at the Front Porch | 2:00 pm to 11:55 pm | The Front Porch in Ogunquit | |
| Jazz Sundays at the Bitter End | 4:00 pm to 7:00 pm | The Bitter End in Wells | |
| Raise the Bar Trivia at Bramhall Speakeasy in Portland | 7:00 pm | FREE | Bramhall Portland |
| Dueing Divas | 8:00 pm | $25.00 | Mainestreet |
| Karaoke Queen | 9:00 pm | Mainestreet |