It’s a busy month with a lot going on. To help you decide what to do, we picked one event for each day this month to take the guesswork out of how to make the most of your October.

Tuesday, October 1 

Underground Comedy at The Big Hunt

Join the funniest people in DC for a night of free local comedy. There’s no cover or drink minimum at this show, so you can relax and enjoy a great night of standup at your own pace. (The Big Hunt // 8-10 p.m. // FREE)

Wednesday, October 2

Wine Wednesday!

Benjamin’s on Franklin features half off all wines on their menu today, so it’s the perfect time to branch out from your usual red or rosé and find a new favorite, guilt-free. (Tastemakers DC // 4-11 p.m. // FREE to attend)

Thursday, October 3

The Head and the Heart

Indie folk hitmakers The Head and The Heart haven’t stopped gaining momentum since the release of their self-titled album in 2011. They stop in D.C. to celebrate the release of this year’s Living Mirage, and their energetic live shows are not to be missed. (The Anthem // 6:30 p.m. // $54.50+)

Friday, October 4 – Saturday, October 5 

Unite the District Fest

This expansive festival is hosted by D.C. United and allows you to experience Audi Field on a whole new light. Enjoy food tastings, beer samplings, live music and so much more all at the field. (Audi Field // various times // $20-$35)

Sunday, October 6

D.C. United Pre-Game Oktoberfest Happy Hour

Enjoy the last game of the season in style with this pregame sendoff celebration. Your ticket includes admission to the game vs. FC Cincinnati, one free beer and DC Fray drink specials. (Audi Field // 2:30-4 p.m. // $25)

Monday, October 7

Pop-Up Magazine

This creative storytelling show uses multimedia formats to tell important stories in front of a live audience for fresh takes on new topics. This edition is “The Escape Issue.” (Lincoln Theatre // 6:30 p.m. // $29+)

Tuesday, October 8

Beer Dinner: Go Big or Go Home

This beer dinner is a celebration of Belga Cafe’s 15th anniversary. Join them for traditional Belgian bites and hard to find traditional Belgian beers, of course. (Belga Cafe // 6:30 p.m. // $76.96)

Wednesday, October 9

Cleo Wade: Where to Begin

Poet Cleo Wade’s new book comes out just the day before she’ll come to DC to celebrate poetry and community. Come hear her speak and receive a copy of her new book for double the enlightenment! (Eaton Workshop // 7:30-8:30 p.m. // $25)

Thursday, October 10

Hyatt Centric Arlington Acoustic Concert Series: Chris Cassaday

Where can you enjoy happy hour specials like delicious discounted snacks, $6 draft beers and house wines and $7 house spirits, plus live music from local folk-blues artist Chris Cassaday? At the Key Bridge Terrace, of course. Grab your friends and start your weekend a little early! (Hyatt Centric Arlington // 5-7 p.m. // FREE)

Friday, October 11

Silence The Violence – Benefit Concert

Katy Perry, Norah Jones, Mavis Staples, The Celebration Gospel Choir and Jeremy Elliot all take the stage in support of the David Lynch Foundation, which brings the health and healing benefits of transcendental meditation to those who need it most. (The Anthem // 5:30 p.m. // $50+)

Saturday, October 12

Bring a Guitar to the Bar: Battlecross, Gloom, Eyes of the Nile

Join bands Battlehouse, Gloom No Tomorrow and Iron Maiden tribute band Eyes of the Nile as they rock out in support of the Witt Black Music Foundation’s 3rd Annual Bring a Guitar to the Bar Fundraiser. You can also enjoy craft beer, tacos and raffle prizes. Donations of gently-used guitars for at-risk kids enrolled in the Foundation’s guitar classes are also being accepted at the door. (Atlas Brew Works // 6:30-11 p.m. //$15)

Saturday, October 12 – Sunday, October 13

All Things Go Fall Classic

Union Market’s Dock 5 is transformed into the hottest music venue, as can’t-miss acts like CHVRCHES, COIN, Betty Who and more take the stage. (Union Market //  Various Times + Ticket Prices)

Monday, October 14

Natasha Bedingfield

The rest may still be unwritten (hah) but one thing’s for sure: you don’t want to miss British singer-songwriter Natasha Bedingfield’s return to the stage this fall. I’m willing to bet you loved all her best early 2000s bops, too. (Lincoln Theatre // 6:30 p.m. // $35+)

Tuesday, October 15

David Sedaris

Perhaps the most iconic satirist and humorist in recent history, Sedaris brings his special kind of wit and wisdom for a special night in the district. (The Kennedy Center // 8 p.m. // $39+)

Wednesday, October 16

Speed Dating at Pinstripes

Put down your phone and look up! The love of your life (or maybe your new BFF) could be right in front of you at Fray’s latest speed dating event. In addition to enjoying the lovely company of all your fellow speed daters, you’ll enjoy food, drinks, extended happy hour and the opportunity to win great raffle prizes. This is a 21+ event. (Pinstripes // 7 p.m. // $25)

Thursday, October 17

Avenir Pumpkin Festival 

Join for live music, a beer garden, games and pumpkin decorating! This festival is the perfect way to celebrate the fun and festive season that is fall. (The Shops at Avenir Place // 5-8 p.m. // FREE to attend, $10 beer garden admission)

Rosslyn Cider Fest

Sample ciders from Wild Hare Cider, Winchester Cider Works, Lost Boy Cidery, Strongbow, Bryant’s Cider and Mt. Defiance Cidery & Distillery. Admission is free and $15 gets you 10 tasting tickets. You can also buy full size bottles from your favorite cideries, as well as beer and wine. (Gateway Park // 4-8 p.m. // free-$15)

Friday, October 18

STABLE Grand Opening Soiree

Join STABLE, whose mission is to strengthen Washington, DC’s contemporary visual arts community by providing affordable and sustainable studio space, an engaged, diverse artist community and access to local, national, and international audiences through partnerships, programming and exhibitions, in their grand opening celebration! Meet the space’s artists and partake in drinks and dancing. (STABLE // 8-11:30 p.m. // $30)

Saturday, October 19

Halloween Scavenger Hunt at Balance Gym

Haunt your way through DC at 10 locations with riddles and clues for you to solve and document on Instagram. Your journey will lead you to Dacha Navy Yard, where you’ll find prizes and a spooky celebration! (Balance Gym // 9 a.m. // $16.66)

Sunday, October 20

New Kitchens On The Block Part 6

Try 10 of DC’s most anticipated restaurants before they open doors to the public. Part 6 includes Maialino Mare by restaurateur Danny Meyer and chef Rose Noel, Hi/Fi Taco by chef Nate Anda, Cranes by chef Pepe Moncayo, Tabla by Jonathan and Laura Nelms and many MANY more, plus Erik Bruner-Yang will debuting his first menu for &pizza since becoming their executive chef. (Mess Hall // various times + ticket prices)

Monday, October 21

Day of the Dead Kick Off Party

Enjoy Oyamel tastings plus bites from other great locations as they kick off Day of the Dead celebrations and honor Mexican-American musician Ritchie Valens. (Oyamel Cocina Mexicana // 6-9 p.m // $60)

Tuesday, October 22

The Office Halloween Episodes Trivia at Pinstripes Georgetown

Flex your skills as a true fan of The Office with trivia of all Halloween themed episodes of the classic sitcom. Don’t forget to come dressed as your favorite character or your favorite character’s costume! (Pinstripes // 7-9 p.m. // FREE)

Wednesday, October 23

Slash Run Annual Spooky pumpkin painting party!

All ages are welcome to this annual pumpkin painting celebration, so come get creative with some spooky arts and crafts. Stick around for a scary movie screening at the end of the night! (Slash Run // 5-11 p.m. // $10)

Thursday, October 24

Capital Book Fest

Calling all book lovers! Add to your stash as you shop over 12,000 gently used books, CDs and DVDs. As if all of them being priced $6 and under, all books are provided by Carpe Librum, a used, donation-based bookstore benefiting the DC nonprofit Turning the Page. (Woodrow Wilson Plaza // 10 a.m. – 6 p.m. // FREE) 

Friday, October 25

Open Bar Halloween Bash at Grand Central

This Halloweekend celebration includes an open bar and costume contest with up to $100 worth of prizes available to win! Your ticket includes rail cocktails, house wine and beer at an open bar. Includes tunes by a live DJ, too. (Grand Central // 8-11 p.m. // $26.66+)

Saturday, October 26

EIGHTIES MAYHEM – 80’s Halloween Dance Party

Enjoy the best 80s jams and a Ghostbusters themed party in the main room, and the Red Room (a.k.a. REDRUM) for Halloween. Featuring appearances by DJs Steve EP, DJ Missguided and Killa K. (Black Cat // 9 p.m. // $15) 

Sunday, October 27

Tegan and Sara

Indie stars and sisters Tegan and Sara are celebrating the release of their book “Hey, I’m Just Like You” with this intimate “solo, acoustic and interactive” tour. $1 per ticket sold will support Tegan and Sara Foundation, which fights for health, economic justice, and representation for LGBTQ+ girls and women. (The Lincoln Theatre // 7 p.m. // $40.50)

Monday, October 28

Jonsi & Alex Somers: Riceboy Sleeps with Wordless Orchestra

Jonsi is perhaps best known as a member of the iconic Icelandic band Sigur Ros, but fans of the band or his solo work won’t want to miss the first ever performance of the album Riceboy Sleeps alongside Alex Somers and the Wordless Orchestra. (Lincoln Theatre // 6:30 p.m. // $39.50+)

Tuesday, October 29

Hocus Pocus Trivia at Pinstripes Georgetown

Grab your cape and broom and get ready to represent your coven at this special edition trivia night dedicated to this classic Halloween flick. (Pinstripes // 7-9 p.m. // FREE)

Wednesday, October 30

Dan Deacon DJ Set

Join Baltimore’s own Dan Deacon for a free and festive DJ set to kick off your Halloweekend in the best of spirits (get it?). Dance the night away with Deacon and his pioneering electronic sounds. (U Street Music Hall // 10:30 p.m. // FREE)

Thursday, October 31

CAMP at the LINE with Whitman-Walker Health

This Halloween edition of CAMP in supports of Whitman-Walker Health with performances by the queens of GAY BASH DC, costume contests judged by the Whitman-Walker team and more. Your ticket includes a donation in support of Whitman-Walker Health and a welcome cocktail, too! (The LINE DC // 7-11 p.m. // $15) 

What are you most excited for this October in DC? When you’re out hitting up your favorite Oktoberfest or fall activity or Halloween party, don’t forget to tag #FrayLife #DCFray in your social posts.

Want to spend some of this month outside? Hit up one (or all) of these hiking trails that don’t require you to leave DC!