[ Monthly Roundup / October 2026 ]
October Around Here: Things to Do in Milford
The Milford, Pennsylvania area edition. A film festival, a downtown tasting day, harvest festivals, the pooch parade, and Halloween week in the Delaware Valley.
[ About This Edition ]
This month's roundup covers the Milford, Pennsylvania area only: Milford itself plus the surrounding Delaware Valley communities like Dingmans Ferry and Matamoras. A separate Warwick, NY edition also publishes this month, so if you are planning trips between the two regions, check the Warwick roundup too. Every entry below was verified for 2026 against the event organizers, venue calendars, the Borough of Milford, Milford Presents, the Pike County Chamber of Commerce, Grey Towers National Historic Site, PEEC, and local nonprofit calendars.
October is peak foliage season here, and the calendar leans into it. The anchor weekend is Columbus Day weekend: the Black Bear Film Festival runs Friday, October 9 through Sunday, October 11 across the Milford Theater and venues around town, while Saturday, October 10 brings both Toast to Milford downtown and the Harvest Festival at PEEC in Dingmans Ferry. Later in the month come the Halloween Pooch Parade, an afternoon with Edgar Allan Poe at Grey Towers, and a stage whodunit at the Milford Theater heading into Halloween.
[ The October Calendar ]
Events, organized by date
Full Moon Hike at PEEC
Thursday, October 1, 7:30 to 9:00 p.m.
Pocono Environmental Education Center, 538 Emery Road, Dingmans Ferry, PA
A guided evening hike under the Harvest Moon through the grounds around PEEC, the National Park Service's education partner in the Delaware Water Gap. It is a relaxed walk suited to fall night skies; $5 per person, and it is listed on both the PEEC and Pike County Chamber calendars.
Learn moreFungus Among Us at PEEC
Saturday, October 3, 10:00 a.m. to noon
Pocono Environmental Education Center, 538 Emery Road, Dingmans Ferry, PA
A naturalist-led program on spotting and identifying the mushrooms and other fungi that flourish in the October woods, using identification apps and logging observations. It is a $5 program best suited to curious hikers; registration is on the PEEC site.
Learn moreLaurel Hill Burial Ground Walk at Grey Towers
Saturday, October 3, walk sessions at 11:00 a.m. to 12:30 p.m. and 2:00 to 3:30 p.m.
Grey Towers National Historic Site, 151 Grey Towers Drive, Milford, PA
A dramatic production in the hillside cemetery at Grey Towers: actors in period dress give first-person readings at the gravesites of figures connected to the Pinchot estate. Ticketed, with two sessions on the same morning and afternoon; the Grey Towers Heritage Association runs these atmospheric walks each year around this time.
Learn moreBlockbusters Live in Concert! at the Milford Theater
Saturday, October 3, 8:00 p.m.
The Milford Theater, 114 E. Catharine Street, Milford, PA
An orchestral tribute concert of blockbuster film music on the historic Catharine Street stage, the kind of live show the theater runs between its film series. Tickets go through the official theater pages.
Learn moreClassic Film: The Lady Eve (1941) with John DiLeo
Sunday, October 4, 4:00 p.m.
The Milford Theater, 114 E. Catharine Street, Milford, PA
The Milford Theater's Sunday classic series opens October with Preston Sturges' screwball comedy "The Lady Eve" (1941), introduced with a Q&A by film writer John DiLeo. Tickets are on the official theater pages.
Learn moreBlack Bear Film Festival, 27th Annual
Friday, October 9 through Sunday, October 11, 2026
The Milford Theater, 114 E. Catharine Street, plus showcase venues around Milford including Cafe Wren, the Columns Museum, Log Tavern Brewing, the John H. Wallace House, TriVersity, and Hotel Fauchere
Milford's signature October weekend and one of the region's fixtures: three days of independent film built around the Milford Theater, with opening night Friday and all-day screenings Saturday and Sunday. The main screenings are ticketed through the festival; showcase screenings at the town's galleries, breweries, and historic venues are generally free. A Film Salon at Good Shepherd Episcopal Church, 110 W. Catharine Street, programs shorts, documentaries, student films, experimental work, and animation in themed blocks. The 2026 lineup is published on the festival site as it is finalized.
Learn moreFall Harvest Family Camp Weekend at PEEC
Friday, October 9 (arrival from 2:00 p.m.) through Monday, October 12 (departure by 2:00 p.m.)
Pocono Environmental Education Center, 538 Emery Road, Dingmans Ferry, PA
The long Columbus Day weekend camp package at PEEC: three nights of lodging and meals (Friday dinner through Monday lunch), outdoor adventures, and hands-on fall programming. The adult rate is about $270 with child, commuter, and day rates available, and registration is required on the PEEC site. It is the center's big autumn camp weekend, and it spills right into the Saturday Harvest Festival.
Learn moreToast to Milford
Saturday, October 10, about 10:00 a.m. to 8:00 p.m.
Downtown Milford, along Broad and Harford streets
The downtown fall tasting day from Milford Presents: shops, restaurants, galleries, and businesses across town offer complimentary nibbles and sips, from wine and sangria to baked goods and small plates. It is the borough's second-Saturday gathering for the month (the evening Milford After Dark stroll follows), and a straightforward way to cover the Milford dining and shop scene in an afternoon. The participating-business list is posted on the Milford Presents site close to the date.
Learn morePEEC Harvest Festival
Saturday, October 10, 11:00 a.m. to 4:00 p.m.
Pocono Environmental Education Center, 538 Emery Road, Dingmans Ferry, PA
PEEC's annual Harvest Festival: hands-on activities, conservation exhibits, vendors, crafts, food, and music out on the center's grounds, with $5 per car admission (cash preferred) and no registration needed. It is the free-form, drop-in kind of event the center does well, and it sits on the same day as Toast to Milford, so a two-stop day is easy.
Learn moreMostly Beethoven: Kopelman, Rostad, Feigelson Trio
Sunday, October 11, 3:00 to 4:30 p.m.
Grey Towers National Historic Site, 151 Grey Towers Drive, Milford, PA
A ticketed chamber concert at Grey Towers with violinist Mikhail Kopelman, violist Kirsten Swanson Rostad, and cellist Yehuda Hanani, anchored in Beethoven. Note that there is no open house at the estate that day; 11 a.m. and noon guided mansion tours only, so plan for the concert rather than a full estate visit. Tickets are on the Grey Towers Heritage Association pages.
Learn moreStar Party at PEEC
Friday, October 16, evening (check the PEEC calendar for the start time)
Pocono Environmental Education Center, 538 Emery Road, Dingmans Ferry, PA
An interactive planetarium lesson followed by telescope viewing of the October night sky, about $10 per person. The sky is worth it this month: the Orionids meteor shower peaks in late October, and the darker skies around the Delaware Water Gap make for good viewing. Registration is on the PEEC site.
Learn moreClassic Film: And Then There Were None (1945) with John DiLeo
Saturday, October 17, 4:00 p.m.
The Milford Theater, 114 E. Catharine Street, Milford, PA
A Saturday-afternoon classic: the 1945 adaptation of Agatha Christie's "And Then There Were None," introduced with a Q&A by film writer John DiLeo. It pairs well with the whodunit stage production coming to the same stage two weeks later.
Learn moreHalloween Pooch Parade
Saturday, October 24, afternoon (times posted on the Milford Presents event listing)
Downtown Milford, Broad Street, Milford, PA
Milford Presents' costume parade for dogs through downtown Milford, the borough's lighthearted kickoff to Halloween weekend. Recent editions have drawn costumed canines of every size down Broad Street; the exact 2026 times are confirmed on the Milford Presents listing closer to the date.
Learn moreAn Afternoon with Edgar Allan Poe at Grey Towers
Saturday, October 24, 1:00 to 2:00 p.m.
Grey Towers National Historic Site, 151 Grey Towers Drive, Milford, PA
The Grey Towers Heritage Association's Halloween-season tradition: a dramatic reading of Poe's stories and poems by the American Readers Theatre. It is ticketed, aimed at ages 13 and up, and seats are limited, so it is one to reserve ahead. A fitting pairing with the Pooch Parade downtown earlier in the day.
Learn moreMurder on the Orient Express, Stage Production
Friday, October 30, 7:30 p.m., and Saturday, October 31, 1:00 p.m. (the run continues Sunday, November 1 at 2:00 p.m.)
The Milford Theater, 114 E. Catharine Street, Milford, PA
Agatha Christie's classic murder mystery comes to the Milford Theater stage as a full production over Halloween weekend, with a Saturday afternoon matinee on the 31st. It is the theater's annual live theater slot, and tickets are through the official theater pages.
Learn more[ Around Here Picks ]
Five to plan around this month
-
OCT 9-11 • MILFORD THEATER & TOWN
Black Bear Film Festival
Milford's annual film weekend: opening night Friday at the Milford Theater, all-day screenings through Sunday, and generally free showcase screenings at galleries, breweries, and historic venues around town. See the full entry above.
-
OCT 10 • DOWNTOWN
Toast to Milford
The downtown fall tasting day, with complimentary sips and nibbles at businesses along Broad and Harford, followed by the evening Milford After Dark stroll. One relaxed day on foot.
-
OCT 10 • DINGMANS FERRY
PEEC Harvest Festival
Hands-on activities, vendors, crafts, food, and music at the environmental education center, $5 per car with no registration. The same day as Toast to Milford, so you can do both.
-
OCT 24 • HALLOWEEN KICKOFF
Halloween Pooch Parade
Costumed dogs parade down Broad Street in Milford Presents' annual pre-Halloween tradition, with the afternoon Edgar Allan Poe reading at Grey Towers filling out the same day.
-
OCT 24 • GREY TOWERS
An Afternoon with Edgar Allan Poe
A dramatic reading of Poe by the American Readers Theatre in the estate's Halloween-season tradition. Ticketed and limited, so reserve early.
[ Recurring Events ]
Every week this month
Milford Farmers Market
Sundays, 10:00 a.m. to 1:00 p.m., through October 25 (October dates: 4, 11, 18, 25)
Local produce, baked goods, and vendors in the Key Food parking lot at 501 West Harford Street, rain or shine. October is the last full month of the season before the market closes for winter.
Market detailsPike County Public Library programs
Throughout October, at the Milford Main Library, 119 E. Harford Street, and the Dingman Township Branch, 100 Bond Court, Dingmans Ferry
Recurring weekly programs include PreSchool Storytime, Books & Babies, Mahjong with Friends, and the Crafter's Circle, plus book clubs and genealogy meetups. The library publishes the full month on its own calendar.
Library calendarMilford After Dark
Second Saturday evenings, April through November; the October edition is Saturday, October 10
Shops and galleries along Broad Street stay open later for evening browsing. In October it lands the same day as Toast to Milford, so confirm the evening's hours with Milford Presents before you go.
Milford Presents eventsGrey Towers guided tours
Fridays through Mondays, 11:00 a.m. mansion tours, plus a ticketed first-floor museum open house 1:00 to 3:00 p.m., through November 1
The Pinchot estate's guided season continues through early November, with the Laurel Hill Burial Ground and grounds open dawn to dusk year round. Purchase tour tickets at the visitor center from 10:30 a.m.
Grey Towers visit infoPEEC Thanksgiving Pie Sale
Orders open October 1 and are due by November 16; pies are about $15
PEEC's seasonal pie sale (pumpkin, apple, blueberry, and peach) opens its order window this month. Order early for the Thanksgiving table.
PEEC calendar[ Family & Community ]
Gatherings, kid-friendly programs, and community events
- PEEC Harvest Festival (Oct 10): hands-on activities and conservation exhibits on the center's grounds, $5 per car, no registration.
- Fall Harvest Family Camp Weekend (Oct 9-12): the long-weekend camp package at PEEC with lodging, meals, and outdoor programming.
- Halloween Pooch Parade (Oct 24): the downtown costume parade for dogs, presented by Milford Presents.
- Borough trick-or-treating (Oct 31): the Borough of Milford posts its official Halloween trick-or-treat hours for the 31st on its website early in October, so check there before planning the evening route.
- Black Bear Film Festival Film Salon (Oct 9-11): shorts, student films, animation, and experimental work in themed blocks at Good Shepherd Episcopal Church, generally free alongside the main festival.
- Pike County Public Library storytimes: PreSchool Storytime and Books & Babies run weekly at the Milford and Dingman branches all month.
[ Outdoor & Seasonal ]
Getting out in peak color
October is when the Delaware Valley peaks, and the waterfall trails and overlooks near Milford are the draw. Raymondskill Falls, the tallest waterfall in Pennsylvania, and the boardwalk paths at Dingmans Falls both run through the Delaware Water Gap National Recreation Area, with trails open daily through the fall. The park posts current conditions and any ranger-led programs on its official calendar. nps.gov/dewa
The month's night-sky programming at PEEC is a good seasonal pairing: the Full Moon Hike on October 1 and the Star Party on October 16, with the Orionids meteor shower peaking in the third week of the month. Both are modestly priced and registration is on the PEEC site.
The Grey Towers grounds, including the Laurel Hill Burial Ground, stay open dawn to dusk all month, and the estate's guided mansion tours run Fridays through Mondays. The October 3 burial-ground walk and the October 24 Poe reading are the ticketed highlights of the month there.
The Milford Farmers Market finishes its 2026 season on Sunday, October 25 at 501 West Harford Street, so late month is the last chance for the season's local produce, baked goods, and vendors before the winter break.
New to the area? Our New to the Area guide covers what life is like around Milford and the Delaware Valley, and the Milford community guide goes deeper into the history, dining, shopping, and annual events. The Milford area events page carries the year-round event calendar, and the monthly roundup archive holds every past edition.
Event details can change, including dates, times, locations and admission requirements. Please confirm details with the event organizer before heading out.