Gloria’s local guide · October 2026
Fall festivals, seaside celebrations, Halloween outings and market mornings across Maryland & Delaware. Find your next “let’s go!”
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48 outings · October 2026
🌽 Pumpkins & farms
Throughout October, 2026
Mon–Sat 10 am–4:30 pm · exit by 5 pm
📍 1919 Allabands Mill Road
Make room for a farm day full of autumn atmosphere.
See organizer for tickets
Closed Sundays. Season continues through November 7; picking and activity availability can change.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 1, 8, 15, 2026
Thursdays 3–7 pm · ends Oct 15
📍 2275 Pulaski Highway
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍂 Festivals
Oct 2–3, 2026
Fri 5–7 pm · Sat noon–4 pm for main activities
📍 Downtown Easton / Thompson Park
A downtown celebration with performances and family activities.
Free main event
Associated craft fairs and car shows have separate hours.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍂 Festivals
Oct 2–3, 2026
Activity times vary; check organizer
📍 East Coast Garden Center, 30366 Cordrey Road
Kick off October with a garden-center fall celebration.
See organizer for admission details
The public listing spans October 2 at 8 am to October 3 at 4 pm; that is not a continuous overnight event. Confirm the activity schedule.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Chamber listing ↗🍎 Farmers markets
Oct 2, 9, 16, 2026
Fridays 2–6 pm · ends Oct 16
📍 3700 Limestone Road
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 2, 2026
Oct 2, 3:30–7:30 pm · season finale
📍 735 Mapleton Avenue
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
⛵ Waterfront
Oct 3, 2026
11 am–2 pm
📍 1812 Memorial Park
Celebrate Lewes’s maritime heritage with a waterfront visit.
Free activities
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🌽 Pumpkins & farms
Oct 3, 4, 10, 11, 17, 18, 24, 25, 31, 2026
10 am–6 pm
📍 6521 Holter Road
Corn maze, hayrides and farm animals make a full fall day.
Paid weekend admission
Last hayride is listed at 5:30 pm. Use the date selector on the organizer site.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍂 Festivals
Oct 3, 4, 10, 11, 17, 18, 24, 25, 2026
10 am–7 pm
📍 Revel Grove, Crownsville
Trade everyday October for a village of costumes, performers and artisan stalls.
Paid tickets
Buy tickets online; no ticket sales at the gate.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Tickets ↗🌽 Pumpkins & farms
Oct 3, 4, 10, 11, 17, 18, 24, 25, 31, 2026
Sat 10 am–7 pm · Sun 10 am–6 pm
📍 Milburn Orchards, Elkton
Plan a farm outing with autumn activities in the BIG BackYard.
See organizer for tickets
Last entry one hour before closing. Outdoor activities depend on weather.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 4, 10, 11, 17, 18, 24, 25, 31, 2026
Sat 7 am–noon · Sun 9 am–noon
📍 Riva Road & Harry S. Truman Parkway
Pick a weekend morning for a local-food stop.
Shopping purchases extra
Saturday and Sunday sessions have different opening times.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 9 am–noon
📍 1004 N. Park Drive
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 8 am–noon
📍 Fountain Park
Make a local-food stop part of a historic-town visit.
Shopping purchases extra
Year-round Saturday market.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 8 am–noon
📍 114–126 N. Harrison Street parking lot
Pair your market basket with an Easton morning out.
Shopping purchases extra
Year-round Saturday market; rain or shine.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 4, 10, 11, 17, 18, 24, 25, 31, 2026
Sat & Sun 8 am–4 pm
📍 10567 Coastal Highway
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 9 am–noon
📍 Lewes Elementary School, 820 Savannah Road
Shop local in the market’s fall location.
Shopping purchases extra
Fall season runs October 3–December 5. This is not the summer park location.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 9 am–1 pm
📍 211 Delaware Street
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Off-season Saturdays 9 am–noon
📍 White Horse Park, 239 Ocean Parkway
A convenient coastal Saturday market stop.
Shopping purchases extra
The listing’s seasonal description says 9 am–noon for fall/winter, while its heading shows summer hours. Confirm with the market.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 8 am–noon; confirm before visiting
📍 South Walnut Street / Riverwalk area
Shop the downtown market and make time for a riverwalk stroll.
Shopping purchases extra
The city’s 2026 listing and organizer’s Market Happenings page say 8 am–noon. Other pages show different hours; confirm with Downtown Milford.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
City October listing ↗🍎 Farmers markets
Oct 3, 10, 17, 24, 31, 2026
Saturdays 8:30–11:30 am
📍 206 S. Talbot Street public parking lot
Shop the morning market before exploring town.
Shopping purchases extra
2026 season ends November 21. Rain or shine; adjacent parking is free.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎈 Community
Oct 4, 2026
10 am–3 pm
📍 Hugh R. Sharp Campus, 1044 College Drive
Touch tanks, ship tours and hands-on science turn curiosity into a family outing.
See organizer for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
2026 event announcement ↗🍎 Farmers markets
Oct 4, 11, 18, 25, 2026
Sundays 7 am–noon
📍 Holliday & Saratoga streets, under I-83
Start Sunday with fresh food and city-market energy.
Shopping purchases extra
April–December season. Rain or shine; pets are not permitted.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 4, 11, 18, 25, 2026
Sundays 9 am–1 pm
📍 Downtown: Pitts, Commerce and Main streets
A Sunday morning of local food and downtown browsing.
Shopping purchases extra
May–October season; held rain or shine.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 4, 11, 18, 25, 2026
Sundays noon–3 pm
📍 32165 Winery Way
A Sunday market outing at the vineyard.
Shopping purchases extra
The state’s 2026 guide lists an October 25 season end. The vineyard page uses a general mid-October description; confirm late-season dates.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
2026 market guide ↗🍎 Farmers markets
Oct 6, 13, 20, 27, 2026
Tuesdays 5–8 pm
📍 413 S. Bedford Street
Shopping purchases extra
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍎 Farmers markets
Oct 6, 13, 20, 27, 2026
Tuesdays 10 am–2 pm
📍 2026 state guide: Convention Center lot, 229 Rehoboth Avenue
Tuesday is market day through October 27.
Shopping purchases extra
Location needs confirmation: the 2026 state guide lists the Convention Center lot, while the market website still lists Grove Park. Check with the market before leaving.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Market website ↗🍺 Food & drink
Oct 7–11, 2026
Restaurant hours; special activities vary
📍 Ocean View Brewing, 85 Atlantic Avenue
An oyster-themed week with seasonal food and drink specials.
Food and drinks purchased separately
Check the restaurant for daily service hours and individual activities.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
⛵ Waterfront
Oct 8–11, 2026
Daily hours: see show schedule
📍 City Dock / Ego Alley
Tour the waterfront and explore the world of powerboats.
Paid tickets
Adult general admission listed at $32; preview-day pricing differs. Advance tickets recommended.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Show website ↗🍂 Festivals
Oct 9–10, 2026
Fri from 4 pm · Sat from 9 am; activities vary
📍 Downtown Bridgeville
A Sussex County fall tradition celebrating apples, scrapple and community fun.
See organizer for admission details
Festival schedule extends into the evening; some Saturday vendors close at 4:30 pm. No pets.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Full schedule ↗🍺 Food & drink
Oct 9–10, 2026
Fri 5–10 pm · Sat noon–5 pm
📍 Pemberton Historical Park
A fall tasting weekend with craft beer and entertainment.
Paid tickets
Regular drinking ticket $43; non-drinking ticket $13. Early pricing ends October 2 at 5 pm. Check age rules.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎈 Community
Oct 10, 2026
8 am–2 pm
📍 Historic downtown Berlin
Spend a crisp fall morning among classic cars and downtown shops.
See organizer for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎨 Arts & shopping
Oct 10–11, 2026
9 am–5 pm
📍 Thurmont Community Park / town
Make a foliage-season day trip for handmade crafts and festival shopping.
Free entry; parking fees apply
Held rain or shine. Farther afield than the coastal corridor.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
⛵ Waterfront
Oct 10, 2026
10 am–3 pm
📍 Commercial harbor, Sunset Avenue
Explore the working waterfront and its maritime traditions.
See organizer for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎨 Arts & shopping
Oct 13, 2026
5 pm · end time not published
📍 Bethany Beach Town Hall
A seasonal history talk: Tales of the Tombstone Whisper.
See town for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Town October flyer ↗⛵ Waterfront
Oct 15–18, 2026
Daily hours: see show schedule
📍 City Dock / Ego Alley
A harbor full of sailboats makes a beautiful October outing.
Paid tickets
Adult general admission listed at $32; preview-day pricing differs.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Show website ↗🎷 Music
Oct 15–18, 2026
Performance times vary
📍 Multiple venues in the coastal area
Build an October night out around a live jazz performance.
Tickets vary by performance
Some venues are outside Rehoboth. Check each show’s location.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
City calendar ↗🍂 Festivals
Oct 17, 2026
11 am–4 pm
📍 Historic downtown Berlin
German music, seasonal bites and a lively downtown afternoon.
See organizer for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍂 Festivals
Oct 17, 2026
1–5 pm
📍 Central Park, Bethany Beach
Bring your October spirit to the town’s seasonal celebration.
Free town programming
The town’s October flyer lists Central Park; older promotional material may show the bandstand.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Town October flyer ↗🎨 Arts & shopping
Oct 17–18, 2026
Daily hours: see organizer
📍 Hagley Museum and Library
Browse handmade work and find something special for the season.
Paid admission; see ticket options
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍂 Festivals
Oct 22–25, 2026
Thu–Sat 10 am–7 pm · Sun 10 am–6 pm
📍 Inlet & Boardwalk
A beachside weekend of music, artisan shopping and festival food.
Free festival admission
Food, shopping and special experiences cost extra.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎃 Halloween
Oct 23–25, 2026
Daily schedule varies
📍 Downtown Rehoboth Beach and area venues
Costumes and seaside Halloween festivities make this a signature fall weekend.
Free and paid activities; check schedule
2026 dates are October 23–25. Individual activities and registration rules vary.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🍺 Food & drink
Oct 23–24, 2026
11 am–7 pm · sampling ends at 6 pm
📍 Ocean City Inlet
Sip your way through a separate ticketed experience during Sunfest.
Ticketed tasting
See organizer for age requirements and ticket options.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎃 Halloween
Oct 24, 2026
10 am–1 pm
📍 Stephen Decatur Park
Costumes, treats and big trucks: little goblins welcome.
Free admission
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎃 Halloween
Oct 24, 2026
Festival 4–9 pm · parade at 7 pm
📍 Patterson Park, near Pulaski Monument
Handmade lanterns light up the park at this community celebration.
Free admission
Parade lineup starts at 6:30 pm. Check the organizer for participation details.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎃 Halloween
Oct 24, 2026
11 am–3 pm
📍 Hagley Museum and Library
Add a museum outing to your Halloween plans.
See organizer for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
🎈 Community
Oct 24, 2026
Noon · end time not published
📍 Central Park, Bethany Beach
Keep the October outing going with a live dog show.
See town for admission details
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Town October flyer ↗🎃 Halloween
Oct 24, 2026
Parade at 10 am
📍 Downtown Bethany Beach
A costume parade for people and pups with plenty of Halloween personality.
Check parade registration / donations
Town flyer confirms the parade start. Visit the organizer for registration, route and weather updates.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Town October flyer ↗⛵ Waterfront
Oct 30–31, 2026
Activity and sailing times vary
📍 Chestertown waterfront
Tall ships and live music bring the waterfront to life.
Free and ticketed activities
Runs October 30–November 1. This guide filters its October dates.
Source checked October 1, 2026. Dates shown are October visits only; seasonal listings may continue into November.
Full schedule ↗Try another day, a nearby town or clear your filters.
