As we continue to roll through the month of October, we have no plans of slowing down anytime soon as far as events are concerned. This weekend is chocked-full with fall festivities once again, and while it’s looking to the chilliest weekend we’ve seen so far this fall, it’s still shaping up to be the perfect weekend for fall events. From the Rehoboth Beach Jazz Festival to Berlin’s annual Octoberfest, from the re-scheduled Ironfest in Cambridge to the Howl-O-Ween Pet Parade in Ocean City, there’s something for everyone to enjoy this weekend:

Fall Restaurant Week

When: October 11-October 25

Where: Ocean City, MD

What: The off-season marks the return of fantastic dining deals throughout OCMD, which is typically kicked off with Ocean City Restaurant Week. Two weeks technically, restaurant week provides diners with specials at participating restaurants. Simply head to the site to find out who’s in this year and what to expect.

Rehoboth Beach Jazz Festival 

When: Thursday, October 15 – Sunday, October 18

Where: Rehoboth Beach, DE

What: The Rehoboth Beach Jazz Festival brings four days of Jazz to Southern Delaware, including some fantastic, internationally-acclaimed acts. Many of the shows are already sold out, but there are still plenty of acts to catch over the next four days across the three stages – Cape Henlopen High School, the Rehobth Beach Convention Center, and Epworth Church. In addition, local bars and restaurants will be host to some great entertainment as well.

Taste of the Town

When: Thursday, October 15, 6pm-8:30pm

Where: DelMarvalous Occasions Inc., Salisbury

What: The Young Professionals of SACC invite you to join them for their biggest networking event of the year, the 8th Annual Taste of the Town. Tickets are $15 at the door and include food samples, desserts, and two drinks. A cash bar will also be available. We’re looking forward to the Chef Competition, which will include some of your favorite Salisbury restaurants such as Roadie Joe’s, The Brick Room, Sushi de Kanpai, Evolution Public House, and Brew River, to name a few.

3rd Friday Downtown Salisbury 

When: Friday, October 16, 5-8pm

Where: Downtown Salisbury

What: This month’s theme is Comicon, so be on the lookout for all things heroic, including the local heroes that keep our community safe. Party Heroes is hosting a costume contest, with two categories, one for adults and one for kids under 12. Plenty more of 3rd Friday fun to be had for all ages – see you there!

Autumn Wine Fest

When: Saturday, October 17 & Sunday, October 18 (11am-5pm)

Where: Pemberton Park, Salisbury

What: Live entertainment, a delicious array of wine, gorgeous scenery…we look forward to the Autumn Wine Fest in Salisbury each year, and for good reason. The two-day wine festival offers samplings from over 20 Maryland wineries, along with live music and local food vendors.

Southern Delaware Wine, Food, and Music Festival

When: Saturday, October 17, noon-4:30pm

Where: Millsboro, DE

What: Our inner foodie, wino, and music lover is amped up and ready to hit this inaugural event. Over 40 wineries from Teller Wines will be on the scene, pairing pours with a fantastic lineup of Delaware restaurants. Local music will accompany the wine and food tastings, including Erin Dickins, Lower Case Blues, Vinyl Shockley, Bryan Russo, and Bruce Anthony. We’ve got our eye on the Touch of Italy gourmet cheese demo…

5th Annual Bark on the Boards

When: Saturday, October 17 (walk starts at 11am)

Where: Rehoboth Beach Boardwalk

What: Grab your pups and head to Rehoboth for the Delaware SPCA’s 5th Annual Bark on the Boards! Hundreds of pet lovers will march along the boardwalk to help the homeless animals of Delaware’s SPCA’s Georgetown shelter. The event will also include refreshments, children’s activities, and vendors.

Berlin Octoberfest

When: Saturday, October 17, 11am-7pm

Where: Downtown Berlin

What: Berlin celebrates Oktoberfest with its own version of the German-themed events, including plenty of food, fun, entertainment and libations. It’s fun for the entire family, with polka and live music, authentic German food and the Rosenfeld’s Jewish Deli food truck, the annual corn hole tournament, a pirate slide and pumpkin painting for kids, and the 1st annual hobby horse steeplechase race.

Corvette Weekend in OCMD

When: Friday, October 16 & Saturday, October 17

Where: Ocean City, MD

What: Corvette enthusiasts will congregate in OCMD this weekend for the annual event, with an anticipated 1200-plus visitors from a far north as Canada and as far south as Florida. Car shows, road rallies, a parade and more!

Cambridge Ironfest

When: Saturday, October 17

Where: Downtown Cambridge, 5-10pm

What: As the IronMan Maryland rolls into town, Cambridge Main Street gears up to celebrate with the spectators and racers for the 2nd Annual IronFest. The last finishers of the IronMan Maryland are expected to cross the finish line up until midnight, which is why downtown restaurants and bars are happily providing a place to cheer on the runners at the turnaround located at the intersection of Gay and Poplar Streets. “There will be something for everyone, and it will all be provided by the people and businesses in this community,” said Hesson. “We aren’t creating a mirage. This is Cambridge, and we know that if we give people the best of what our town is about, they will love it.” Expect plenty of live entertainment, local eats, eclectic vendors, and plenty of Eastern Shore pride.

O.C.Toberfest Howl-O-Ween Pet Parade

When: Saturday, October 17, 1pm

Where: Boardwalk in OCMD

What: We love a good pet parade, especially when it’s on the Boardwalk in OCMD! The parade of pets will include owners and their pooches dressed up for the occasion, with prizes given for best dressed. Feel free to bring pet food or other pet-friendly items as a donation for the Worcester County Humane Society.

American Cancer Society’s Making Strides Against Breast Cancer Run/Walk

When: Sunday, October 18, 9am

Where: Boardwalk in OCMD

What: We love this community-based event that invites all ages to join together for a 5K run and non-competitive walk to raise funds and awareness for the fight against breast cancer. For more information, click here.